Leaders Letter Newsletter

Leaders Letter 199 – Scoring To Win

Dear leaders, have you ever sat in a meeting and stagnated, whether that’s with your team, in middle management or at the senior executive level?

The one way most likely way to move forward for most is parking it and revisiting it. That’s long, frustrating and slows down decision-making. 

Others like to grind it out and then meeting recovery syndrome is brutal and sends shock waves through businesses. 

I prefer scores…

I have a sports background, I played almost every sport I could, I played basketball, tennis, soccer, cricket and even lost a few fights in Muay Thai as a kid. 

Scoring Systems

  • Almost all of these sports have dedicated scoring systems for each version, even when playing soccer with friends you create a score or ongoing system to know who wins and loses.
  • Martial arts are great at scoring, as you know the quality of your opponent by the belt they wear, they are graded and scored regularly. 
  • In MMA (UFC) and boxing they both use scorecards, both disciplines have versions of the same scores but they are private until the end of the fight. Who wins is based on the judges’ scorecards – this is always hotly contested when it is close but a winner comes out of it and has their hands raised at the end.
  • Cricket is a sport where you track every single ball, you have it logged and basically you could understand the momentum shifts, from a bowler losing confidence to a batman hitting their first boundary (like a home run in baseball) and then it’s up to them to concentrate and continue scoring. 

Momentum, Mindset, Winners Mentality 

In tennis, it’s easy to know who is winning, by the game, by the set and by the match. 

My brother and I would basically play until we were too tired to ride back home, but my brother is ultra-competitive and always wants to win, especially when I would go up a set and he would typically come back. 

He was always the better player (pains me to say) but momentum in sports is a huge thing and when I had true momentum I would out-battle his quality advantage and beat him. 

Momentum: This is the same in business. Momentum often swings and beats the incumbent without them noticing and without having a scoring system away from metrics and how they are progressing towards their Northstar metric. 

Winner Mentality: Some of the greatest ever tennis players are naturally gifted and super athletic but the top 1% of the 1% is down to their mindset and having the winner mentality. 

In business solo players like this can struggle to influence enough people to have the same elite winners mentality. 

Scoring To Win

Something you will notice is the importance of winning and the importance of keeping score.  

If you are not keeping a record of the score, how do you know how you are doing? 

Scores in business are often the run rate, the costs or the flow of the business. 

Often we ignore scoring our campaigns, our people and our product performance until layoffs or 9-box exercises are given to us. This is then a hard job and when you need to explain decisions it can be extremely difficult to explain something others understand and accept. 

This is where many businesses can make better decisions by applying scoring and having a scoring system that allows everyone to know the metrics and the guidelines for success.

Audit Scoring 

I always encourage all product teams to audit and audit aggressively. 

By scoring and using an open-to-for-all scorecard. I created a scoring system to apply across the user journey to know where to work and what is going to have to be improved to keep customers happy and remove product decay. 

Do you formally audit and keep score? If not, why not? 

The Exec Netflix Score

At Netflix, they created a scoring system -10 to +10 on big business decisions, this came after their very early call to switch business models to go super early on streaming when a large percentage of customers were DVD only (the famous Qwikster business). 

This is a recent quote from Reed Hastings the co-founder of Netflix from the Tim Ferriss podcast that I love: 

Listen to the full podcast below

My important question for you today is – Do you have your own scoring system? 

This week’s focus action is – Can you make smart decisions by asking your team to score and score regularly? Not like eNPS or other metrics that are too situational.  


  • The best managers energise their teams by person-to-person management and ensuring they have a personalised target that energises them towards success. Everyone is engineered differently, the best managers know this and can press that button. 
  • Whereas, the best leaders can inspire teams of people when the chips are down with a rally cry, or a great way to re-think to move forward or they unlock a way to score others just haven’t seen.

Will a scoring system be that for you? 

Have a great week ahead!


Danny Denhard

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Leaders Letter Newsletter

Leaders Letter 197 – Ask Me Anything Part 2

Dear leaders, this week I am going to answer a few follow-up questions I received this week. Thank you for your thoughtful questions and those who fed back – thank you!

The leadership questions I cover this week to help you include helping with: 

  • You or your colleagues to re-think where they think they are in their careers 
  • Quick wins for leaders wanting to improve their leadership skills 
  • Address challenges within companies 
  • How to build your executive edge (not just your ‘exec presence’)
  • How to reboot your career 
  • You to learn from hard lessons in my career 

Sharing Is Caring: Copy and paste this URL to help a colleague or team member who will benefit from this advice

» If you missed my AMA Part 1 read today 

What are 5 of the hardest lessons you have had to learn from in your career? 

  1. Leaving a workplace can be like a breakup with a long-term partner, everyone has that one former workplace, you can grieve, you will receive some unconstructive feedback, someone will always have something to say about you after you leave, you will receive some nasty comments and you will lose some “friends” in the process. If you feel this could be a case get some help through therapy, this will become more and more common in years to come. 
  2. Words and actions are often so disconnected you have to learn to dissect the words from the actions and drive the change yourself. 
  3. Colleagues will decide between professional friendships and their salary, salary almost always comes first and don’t be surprised. 
  4. A bad manager will put your career backwards if you are under them for six months – they’ll put you back a year. I have had two or three terrible managers and thankfully I learnt to get out in under six months. I thankfully had great people around me to guide me into a move for my mental health. 
  5. A company on the up is great to work in generally, a company on the way down (especially being hidden) can be an impossible company to operate in and personal development is limited

Bonus: However much you look out for your team members, department heads or senior colleagues you won’t be seen as doing enough for everyone

Are there any quick wins for leaders to get better at leadership? 

  • Learn how to present well, from creating a deck (or editing a deck) to presenting with confidence away from reading it word for word, slide by slide  
  • Learn storytelling basics and principles – capture attention and imagination, the more you compellingly tell the story and garner engagement the sooner you will improve as a leader  
  • Hard decisions have to be made – put yourself in a place where you can make hard decisions and know whether this is a quick or long process 

What are the biggest challenges companies are currently facing today, and how do you recommend the company addresses these?

  • Profitability and efficiency targets – hard for most employees to impact directly and have very little visibility. Show staff members how they can move the needle and be more open around performance and ownership. Move away from the spreadsheet view, it’s terrible for storytelling and connecting people to performance  
  • Culture – companies are dealing with social networks dividing people, political unrest and political opinions are being shared more loudly and many feel they have to have a side or pick a side. Aligning any of this and attempting to drive a positive work environment while building a culture around performance is particularly challenging. Unfortunately, I don’t have all of the answers on this one, what I do recommend is creating guidelines around topics for discussion within the work environment. Coinbase and 37Signals (Basecamp) were called out by recommending this at the time (and didn’t execute it well) but there are some valid points in helping to reduce external factors impacting the workspace 
  • Keeping staff happy – while losing colleagues and having to pick up their work. This is common until the headcount is replaced in the old normal but in today’s business landscape, this just isn’t going to happen. This needs leadership to step up, help readjust priorities and remove roadblockers 
  • Hard economy – for many it is tough and it’s hitting them harder than expected, while some big companies are cutting back on perks and some smaller firms are asking staff to return to the office, travel, food and drink prices increased. There is no fix here but there are ways companies can support their staff, help with travel or proactively help with reducing high prices. 

What are the best methods of career progression when you feel your career has stalled? 

  • Go and interview, get the experience back under your belt and understand your worth 
  • Build your own personal development plan – take control, write out the areas you have to improve, you want to improve and the areas you have always wanted to go into and set milestones. One follow-up recommendation: partner up with someone who will keep you accountable – this way you aren’t attempting to do too much and not celebrate the progress 
  • Get more experience – if that means helping other companies, helping a startup, or creating a side hustle you need broader experiences to help restart how you think and how you view your current situation 
  • Start learning again – most people in their career stop learning and stagnate, whether you are a specialist or a generalist you should be able to learn quickly. Reading a recommended book, listening to podcasts, downloading workbooks, signing up for a cohort course, and watching lectures on YouTube are all low-cost ways to learn and ways your company will pay for your development 
  • Write a professional SWOT and highlight where you need to improve and where you have the opportunity to drive your career or gain help driving it forward 
  • Get a mentor – someone who you look up to or people who will share their experiences and help put you first not just tell you how they did things 
  • Get a coach – this is biased advice however a great coach will help improve your skills, help to boost your own confidence and shape your near and long-term future. The best coach won’t just push you, they’ll help to reshape your ‘now, next and future’.  

I have read you need an edge as a leader, what do you recommend?

  • Be known for something important (not just your title) 
  • Be relatable and approachable (this goes a long way with the layers below you)
    Or be unavailable (time-constricted people’s time seems more valuable – don’t be the exec who celebrates with a busy badge of honour) 
  • Operate well under stress – if not you will struggle to drive positive change and the higher you go the more stressful it can become 
  • Be additive not defensive – add more than you create slowdown or stoppers 
  • Have a catchphrase or a look that sticks in people’s minds – this should reflect you authentically but it can also be crafted 

This week’s focus action is to create a list of actions to help you and your leadership development and the steps you will take moving forward and then help your team members create their own plan.

Have a great week and remember to sign up to the newsletter below

Danny Denhard

  • Leaders Letter 199 – Scoring To Win

    Leaders Letter 199 – Scoring To Win

    Dear leaders, have you ever sat in a meeting and stagnated, whether that’s with your team, in middle management or at the senior executive level? The one way most likely way to move forward for most is parking it and revisiting it. That’s long, frustrating and slows down decision-making.  Others like to grind it out and…

  • Leaders Letter 198 – Who Do You Serve & What’s The Prioritisation?

    Leaders Letter 198 – Who Do You Serve & What’s The Prioritisation?

    Dear leaders, who do you serve?  And in what order do you serve them? I remember an all-hands I attended and the EVP stood up and read from a very simple slide: “We serve the shareholders first, then customers second and then the staff”  It stuck with me, I was in a follow-up meeting and…

  • Leaders Letter 197 – Ask Me Anything Part 2

    Leaders Letter 197 – Ask Me Anything Part 2

    Dear leaders, this week I am going to answer a few follow-up questions I received this week. Thank you for your thoughtful questions and those who fed back – thank you! The leadership questions I cover this week to help you include helping with:  Sharing Is Caring: Copy and paste this URL to help a colleague…

Leaders Letter Newsletter

Leaders Letter 194 – The 3 Box Challenge Interview Question

Dear leaders, I’m going to let YOU into a secret, there’s an interview question I love asking, it is one of three questions with challenges I ask to find out the best candidate(s).  

This is an in-interview question, not a challenge to set with any pre-warning. 

If There Were Three Boxes In Front Of You – What Would You Do? 

Here is the breakdown: 

You don’t know what is inside of  

  • Box 1 
  • Box 2 
  • Box 3 

Some Guidelines 

  • You have 30 seconds to view the boxes 
  • You can lift the boxes once 
  • You cannot shake them  
  • You cannot open the boxes or see inside of them – they are padlocked 
  • You can walk around the boxes and look under the table 
  • You cannot ask for the exact contents of the boxes – but there are varying amounts of money inside 
  • You have 5 minutes to complete this challenge – remember to set the timer so there is pressure associated 

Phase 1A

I will let you ask 3 questions to qualify the boxes 


I can give you 3 hints:

— Do YOU pick the questions or the hints? 

Phase 1B: Questions Or Hints 

The 3 hints are: 

  1. 1 sentence to explain vaguely what inside box 1 
  2. Offer you to pay a % of what is inside box 2 
  3. Box 3 needs breaking open 

Readers stop here: Question: What is the best option for you? 

Phase 2: Answer Questions Or Pick 

Answer questions with varying answers. 

Note: Almost all questions will be trying to validate what’s inside the boxes and which is best. 

Which do you pick?


Do you want to carry on qualifying? 

Phase 3: Select Step Forward Or Step Back? 

Ask: (1) Step forward and select a box 
(2) Do you want to step back — if step back ask them if they want to ask 1 more question or select 1 box to be removed. 

Phase 4: Offer A Question

If I were to ask you to start again would you change your decisions so far? 

Phase 5: Box Selection

Ask what box you are selecting and why?  

» So, which box did YOU select? 

Here are 6 presets to make this successful for you and the candidates:

  1. Set the money amounts for each box before the challenges 
  2. Vary these amounts at each interview some candidates share online and it could be gamed 
  3. Set the timers to view “the boxes” and the 5 minutes – many will run out of time 
  4. Have a slide with 3 boxes set up or a set of boxes you can pull out and run through the exercise 
  5. Work out if you are going to let the candidate see the other two amounts 
  6. Money could be £, $, €’s or could be notes, a cheque, a mocked-up bank statement, a USB stick etc – be sure to know the contents and the order of least to most 

I know what some of you are thinking, this is either a clever challenge or a stupid challenge and you might be right, it could be clever and stupid at the same time. The but: you need to understand the candidate and without some form of challenge and working session how do you get to know them? 

Why This Challenge? 

  • The challenge is designed to understand the decision-making process and understand first, second and third-order thinking from your candidates. 
  • One of the biggest challenges in interviewing is to understand your candidates’ working style and decision-making while asking questions 
  • No questions all answers are typically a red flag to me – this is where a gambler and a calculated risk taker are decided. This is on you as the interviewer to understand and bring out of the candidate 
  • This is a collaboration challenge – you learn if they are a collaborator or make their decisions on their own, if they select not to collaborate ask questions on why this was the case. Hint many selfish managers and above will make the decision not to collaborate, understand the engineering behind this 
  • Making a decision in a controllable environment is what they will likely have to undertake week in and week out 
  • You will find out a lot about the candidate’s confidence and conviction 
  • Candidates who think outside the box often get into the box 
  • This challenge doesn’t have a right answer per se and often within business you have to make a hard or what seems an impossible or stupid decision fairly quickly 
  • This challenge is a simple challenge designed to:
    • (1) Challenge the candidate’s mind 
    • (2) Understand if the candidate wants to change their mind and how many times they change 
    • (3) See how the candidate makes up their mind and challenges themselves and you
  • You find out if you would want to work with and trust this candidate in the early phases of working together 
  • If the candidate does not ask about the motive or what’s in the other boxes, do they demonstrate a growth mindset? Or have they decided to move on and not look back…

Why did I share this today? Many interview questions are bland and restrictive and they do not effectively test candidates in a working environment and you do not understand your potential colleagues at an operating level quickly enough. This is why I have 3 questions and challenges to test the candidates and the interviewing team to deeply understand each other and the dynamics moving forward. 

This week’s focus action is to review this challenge and see if you could use the 3-box challenge in your mid to senior candidates and whether you find out enough about your candidates in your interview process. 

Have a great week and I’ll land in your inbox again next week,


Danny Denhard

Missed Any Leaders Letters? Here’s 3 Of The Most Recent To Help You To Become A Better Leader

Leaders Letter Newsletter

Leaders Letter 193 – Is It Time To Reshuffle Your Executive Team?

Dear leaders, how are you and your managers and management team doing? 

It is business week 8 (where has 2024 gone already) and typically you get a pretty good baseline of how things are going, how the business is shaping up and how your team have performed. 

One question that is often asked around now is: 

How do I know when it is time to review your leadership team? 

And connected follow-up question: 

» Is it time to review my management team around you (those who report to you)?

The big question you have to ask yourself is:
How are you performing and how are the relationships and dynamics helping the team and the company progress?  

You might be in one of three situations: 

  1. Leaders like their colleagues but don’t love their output. 
  2. Leaders dislike their colleagues and the team around them but they perform.
  3. Leaders wouldn’t mind if they left and it wouldn’t impact performance. 

If you land with option 1 or option 3 you are ultimately in a place to consider performance plans or a reshuffle. 

Letting go of people you dislike but perform within their role is what makes or breaks leaders and tests your executive chops. 

The Cost & Effects Of Hiring & Firing

Hiring and firing is a core part of being a leader and many struggle with hiring replacements, understanding the demands of their org and then replacing almost like for like or go to an extreme opposite and miss the subcultural impact. 

The Caretaker AKA The Number 2: Others thrive in the firing but the replacements are often not lined up and can take a long time to replace, you are then expecting someone internally to step up and often this will see performance stay as is or improve. 

You are then left in a place with a number 2 who will ultimately have two decisions to make: 

1/Is this number two role enough 

2/ Will this new boss feel threatened and can I learn anything from them to progress my career further? 

Often the ‘Number 2’ will move on and you will be left with a hole and a six to twelve-month window where you will have instability and turbulence.  

Middle management is a tricky place to operate and often when you are in the mid to senior end of your career a new boss coming in to replace your old C-Suite boss is a big swift and has months’ worth of impact on you and the team around you. 

Executive Changes = 24 Months Of Hard Change 

If you notice what happens in many companies, a new CEO comes in, assesses their colleagues and their board and the supporting management team and then makes changes, some make sweeping changes and bring in their people, while others refresh core areas and often make the management team smaller. 

This approach is often about the CEO being successful first not always directly correlated to the business being successful. 

10 Leadership Levels Questions To Consider

There is no one size fits all but here are 10 important themes to consider and bake into your plan (sidenote – always check with legal and HR to ensure you have taken the right legal steps to protect you, the company and the individuals you might be letting go). 

  1. Any Move Is A 2-Year Bet: Don’t make big and rash decisions if you haven’t planned out the next 2 years 
  2. Identify The Right Interim Lead: The next question to ask and answer is: Is there is someone within the team who can and will step up or will there be another exec who is tasked to step up and run dual areas
  3. Thrive Vs Chaos: Some departments thrive in change, while others don’t. Chaos and confusion are never tolerated – find out which the departments are and how you remove any confusion with a timeline of next steps and actions 
  4. Back Up Plans: If you are an exec and department lead understand how you are reshaping a team/discipline lead will impact the business for the next 12 months and have backup plans for additional support, hiring consultants, agencies or reshaping to adding more headcount under the original level will help to get back into the driving seat. You will naturally need to step up and have relationship managers with external vendors to own the alteration  
  5. Sub Culture & Cultural Impact: Culture can be made and broken by hiring and firing mistakes, hiring is more important than firing, if you hire badly you have six months to understand their capabilities and influence and then be confident they are right for the next 12 months 
  6. Popularity: Popular employees being let go sends ripples through businesses, from gossip to direct questions about them and their performance. Understand the impact of these decisions and how you will address this 
  7. Comms Plan & Plan Execution: Communication is key, what you say to the key member of staff you are hiring and firing is critical it stays between you.
    1. Welcoming new senior staff or a shift in operating models requires a well-thought-through comms plan. Time and energy are critical here 
    2. You will need to have a company-wide notice to explain the reasons and what the future looks like clearly. Over-communication and over-sharing lead to questions and a reduction in confidence 
  8. Difference Between Small Biz & Large Orgs: If you are looking to make many changes inside a small business it will reshape quickly, if you are in a mid-sized business it takes longer to understand the impact, in large and enterprise businesses it can be 9-12 months for the effects to come out in the wash 
  9. Talk Of The Town? Big exec firing will lead to external questions and will be the talk of recruitment/headhunter firms, C-Suite groups and industry press. Knowing how to frame the layoff and reshuffle externally is as critical as internal comms. Know internal comms will be shared and screenshotted to be shared across social media and chat apps 
  10. Day 0 Influence: If you want to restart a department’s performance you will have to think about the executive in charge and their relationships and influence over their department. If they have influence and sway you will need to understand how to replicate this, if they don’t think and plan about how you will restart from day 0 of letting them go. 

This week’s focus action is to review if you should reshuffle your exec team, review the list of exec hiring and firing notes and make an action plan on who, what, when, why and how to move forward with reshuffling your executive team. 

Best of luck this week and if you are in doubt ask yourself, if this person were to leave on their own terms what would the plan be, versus letting them go as the leader? 

Thanks and have a great week,

Danny Denhard

Leaders Letter Newsletter

Leaders Letter 192 – How You Will Know You Are On Thin Ice As The Leader

Dear leaders, I have recently written a number of leaders letters that you have told me have resonated with you, from: 

Today’s leadership newsletter will make you take the time to analyse and your improve leadership skills. 

It makes my day when I receive feedback on the newsletters, I will always invite replies to my newsletters, to discuss the topic, and see where you have rolled something out or where you might be struggling and need a quick pointer. 

Since the turn of the year, there has been a theme of replies and they can be bucketed as:   

How Do I Know If I’m On Thin Ice As A Leader? 

Although each environment is slightly different; there are common themes that come up and there should be a series of warning signs you’ll spot or worryingly you could be blind to. 

From experiences here is a breakdown of the standard signs:  

  • Performance
    • Poor company performance 
    • Poor performance from direct reports
    • Bad decisions or poorly timed decisions leads to poor performance 
  • Communications
    • Waiting for everyone else to catch you up on the important updates
    • When you are days behind in communications (email, slack etc) and it impacts how the business operates 
  • Offbeat
    • When you are not in the same rhythm as the company
    • When decisions drive larger heartbeats jumps and is like a shock wave through the business   
  • Stagnation
    • Status quo from your team (if department lead) 
    • Projects and product(s) stagnate from decisions or lack of clarity 
  • Trust
    • Lack of trust among your colleagues 
    • Being uninvited / removed from meetings 
  • Feedback
    • More feedback from colleagues 
    • No feedback from colleagues and direct reports 
  • Discipline
    • HR issues and common HR issues 
    • Team members misbehave as they have seen others being rewarded for these behaviours in previous promotions 
  • Crisis Mode
    • Everything seems to be the highest stake meeting 
    • Everything is urgent or a crisis 

Leaders Duty

There is often a blend of the eight themes above, most often leaders are undone by their miscommunication and the lack of clarity and repetition of their important decisions. It is the Leadership Team’s duty to address the misfiring of the teams below them and build trust between internal customers and external customers constantly. 

Leadership IS

Leadership is incredibly challenging, and making the right and smart long-term decisions comes under the microscope of the business frequently especially the larger the business is, the more investors, advisors and shareholders evaluate you, one shift in the market and you will be under fire. 

Your Decisions To Delivery Hole 

In business leadership roles, there are thousands of ‘micro-decisions’ you make every day as a leader, you make what feels like small decisions and your business then gives them inflated weight, you are often judged on bad decisions part of your core team makes and frequently the disconnection between your leadership team and their department and team heads cause big directional shifts. 


It is how you understand and improve: 

  • What is happening (not just the numbers – this is issue number one of bad leadership)    
  • The behaviours of you and the teams below you – if key individuals are causing the problems or allowing bad behaviours you will need to make hard decisions of keeping and improving them quickly or removing them to ensure improvements 
  • How you got to this situation as a timeline is critical to turning the problems around and addressing the majority of the issues 

Most leaders do not dedicate the time and then the resources to address the issues and core traits within the business, this is what makes the top 10% of leaders. Move into the top 10% and address the issues and audit performance of the business, the teams and the people. Get under the skin and inside the culture of the business to drive positive change within the business. 

This week’s focus action is to: 

  • Short Term: Dedicate the time to audit what is happening and not happening within the business and in your leadership 
  • Mid Term: Create an action committee from around you and your trusted team members to create the next steps and hold everyone accountable 
  • Long Term: Admit things were not perfect and present the actions under the 5 pillars you are changing and why these are changing 

Have a great week stepping up and being the leader you want to be and need to be, I will land in your inbox next week


Danny Denhard

Leaders Letter Newsletter

Leaders Letter 191 – The 11 Core Skills For Great Middle+ Managers

Dear leaders, middle management is either the most rewarding or the hardest career phase.

Middle management should play a critical role within every organisation, unfortunately, many big tech companies have removed the middle manager and the ripple effects of how middle management can be seen is making many companies question the importance of middle managers. 

The Glue & Translator 

I am a huge advocate of the right layers of leadership within businesses, middle managers should be the glue to organisations, middle management should be the area of the business that filters decisions and applies to their team(s) and middle management should translate their plan into the company strategy and then has been able to connect the dots for their team to how they are impacting the business. 

Awareness Of The Business Finances Is Critical 

In today’s business world, if you are not in a place to have a healthy number of middle managers you will likely have a high level of staff turnover and department leads with too many direct reports.  

If you are reading this and think my business needs more middle managers, be fully aware of the financial demands on your business and operational efficiencies that have had to be made to keep several team members over a middle manager. 

If you do not know or struggling to understand this, speak to your leadership team and get under the skin of the business model and dynamics. This is what a good leader will want and shows your potential leadership skills. 

The Good Of Middle Management 

You have likely experienced a great (team or department) manager who was not the most senior within a business, who understood you, knew when you were having a bad day and understood how you liked to be praised and when to provide you feedback.

The Bad & The Ugly Of Middle “Managers”

You could have also experienced the power-hungry middle manager who put themselves first and would play the blame game, blaming everyone around them for bad results, for not evolving and not acknowledging their team when the team does a great job or delivers something that improves company performance. 

Evolution Before Revolution? 

The “role” of the middle manager has not changed too much, however, the demands have escalated particularly in the recent waves of layoffs, from managing small teams to some managing teams of 100 and having limited managers beneath them to support and shield them. 

A middle manager in other businesses has been pushed into more delivery as much as management and this is creating blurred lines. 

Remember, what happens in big tech is often replicated in smaller businesses and aspiring businesses and this creates a big divide between what management is and what are the expectations. 


The Core Skills & Traits For Great Middle Managers

How about I talk you through the best 11 traits and skills I have experienced and witnessed throughout my career and gathered feedback from 1000s of hours of interviews. This will help you to work through what you are good at and what you need to develop. 

  1. Communication – being able to communicate simply, cut through noise and help to set direction with their communication. They also change their communication style based on who they are talking to and on the platforms that make the most sense  
  2. Feedback – have the ability to deliver important feedback whether that is positive or negative. Being able to deliver in-the-moment feedback and creating no-surprise feedback is what makes the difference between a good and bad middle manager 
  3. Skill Development – improving their team members’ skills and improving the teams’ skill base is a vital skill middle managers have and knowing how to improve yourself or recommending training is a key skill  
  4. Time – a skill all the great team and department managers have had is creating time, managing deadlines, creating time to discuss potential problems and issues and managing their time effectively is what only the greatest managers have (particularly important as a team lead or a department head) 
  5. Deep Business Knowledge – the elite middle managers know they have to balance the personal (team members) and the business demands, often being able to inform the team of how the business operates and know good or bad decisions from the team will impact the revenue lines or cost the company 
  6. Motivation – personal and team motivation is often overlooked and underplayed, being able to motivate a team that is struggling with performance anxiety and when the team has lost a team member or headcount has been decreased. 
  7. Empathy – EQ is now widely known as a powerful leadership skill, empathy is a core component of EQ and middle managers have to show empathy, not just to their team members but also to the business. Being empathic to both needs is often overlooked and undervalued
  8. Reduce Headwinds And Create Tailwinds – this is a leadership skill that very few proactively work on, this is a core workstream in my exec coaching, understanding how “leaders” reduce headwinds for their team(s) and for the business, while how to keep the momentum going and create tailwinds, often by motivating their team to keep pushing or keep delivering high-quality work. If you want to be a business leader or go into exec teams one thing that will make you truly stand out is being able to reduce headwinds (get people out of the way, get yourself out of the way, add yourself into a problem you can uniquely solve, add people to problems, kill a part of a project etc).  
  9. Decision Making – some middle managers feel like they cannot make core decisions which is not the case. Decision-making and making hard decisions are part of parcel of your daily life as a middle manager, knowing when to dial up and dial down decisions and escalate decisions is something middle managers have to work on and the best know when to get help or be the help. Something many mature middle managers demonstrate is being able to make smart judgment calls. Judgement calls are decisions being made when you might not have the data but you have a feel for something, this is also part of your management development
  10. Cross-functional Collaboration – the worst middle managers do not and will not play cross-functionally, this is criminal and has a detrimental impact on your team(s) and the business. The best middle managers know cross-functional is key to success, even when the two department heads might not have the best working relationship or often competing for a promotion into the next layer of leadership  
  11. Resiliency – most likely the skill as a middle manager or previous middle manager you will resonate with most, you have to have a high level of resilience as a middle manager, you have the hardest management role within any organisation and you will feel helpless and alone and on other days you will lose people to other opportunities because you invested so much time and energy developing them to the next level of their career.  

The best leaders in the world learn to develop themselves and those around them, the best managers study the art of management and then apply their learnings and teach the painful (and the good) lessons to their team members. 

A great middle manager doesn’t just positively impact their team(s) or department but has a real influence on the business and in unique cases, creates a standard of management for other managers to buy into and apply. 

This week’s focus actions are to 

  1. Re-review the 11 middle management traits and skills 
  2. Evaluate yourself, consider creating a professional SWOT analysis (aka the management SWOT) and 
  3. Work through which you excel and which you have to work on. One running theme you will notice upon doing this is – these traits are true leadership traits and the best CEOs and founders demonstrate these every week. 

Thanks and have a great week ahead, 

Danny Denhard

Leaders Letter Newsletter

Leaders Letter 190 – The Who, What, When, Why, How Of Leading Business To Success

Dear leaders, you may have noticed this week the newsletter is slightly delayed. 

Apologises, I want to be transparent, I have been working on a couple of larger consultancy projects combined with my coaching commitments and I wanted to take a few extra days to land with the usual high-quality newsletter that’s going to add value rather than just a good newsletter that I’m not happy enough with. 

Let’s dive into The Who, What, When, Why, How Of Leading Business To Success.

The Different Ways Of Working Towards Success 

Startup Approach:

  • If you have worked in a startup you would have noticed everything is often thrown together, the idea of strategy and tactics and often blended and sort of everyone’s job. 
  • On the flip side, some startups have more leadership team that says who does what and when and sometimes include “the how” you are going to do it. 
  • Startups win by hitting aggressive targets and getting a lot of buy-in from the teams not always being autonomous and democratic. 

Scaleup Approach:

  • If you have worked in a scaleup, successful businesses know how to split out who does what – when, the why is explained and the how is often left to department leads and they present to the business.
  • Scaleups win by maturing from their previous state, they mature and grow by adding in more processes and taking away the goal(s) is the only thing to hit. Scaleups fail by acting like startups with only startup employees. Sad but true.  

“The Mature Approach”:

  • In mid to large-sized businesses the exec team will say to the business what you need to do to hit a set of big goals and then the discipline leads to controlling the who, the what, the why and the how, the why is often left to the business to explain otherwise the business results will go aray. 
  • Larger companies win by what I call controlled collaboration and being hard on the goals and output but the who and how many are often most flexible. 
  • Middle managers will be critical in some mid to large-sized businesses, and completely redundant (as we have seen in layoffs from Amazon, Meta, Google and many other tech companies) in others. 

No Secret Formula? 

I have worked across the full spectrum of businesses, from small ten-person businesses to larger 5k to 15k-person businesses and there is no perfect one-size-fits-all for the who, the what, the when, the why and the how. There are ways to push the business in the right direction by understanding if it is leadership-owned or leadership-guided. 

Change Is Hard But Necessary

There are, however, businesses that just stick to how they have always done it and top-down (directions from the exec team) that went from being successful to slowly but surely status quo-based businesses that decline and then the point the fingers phase, blaming those underneath them for struggling to make bigger changes or being able to make broader changes to their tech and then hiring more sales doesn’t work and Marketing can’t squeeze another 10% out of a bad Product. 

You lose in business by staying the same and squeezing more and more out of a bad product and badly positioned products. 

This is where trust evaporates within leadership teams and rips through your business when everyone is fully aware of this situation and cannot make any meaningful change because of poor leadership decisions.  

Below is a way to consider the who, what, when, why and “the how of your company”, regardless of how you build your company goals (OKRs or an alternative) 

Leadership Flex 

Leadership is mostly won by: Adding in the right level of guard rails and adding in flex to take ownership if and where required. Flex does include layoffs (Google is spending $700m on severance this quarter alone), removing department leads and finding a blend of the two or (not in recent times) mass hiring to accelerate with market shifts and new opportunities.  

Question for today: “Is our company leadership team giving enough direction or is it providing too much?” What stage are we at and how do we empower or power up our employees to feel part of the driving force behind the business? 

This week’s focus action is to: review The Who, What, When, Why, How Of your leadership teams and proactively drive change throughout your leadership, management and up and comers to keep being successful and drive long-term growth within your business. 

Have a great week and I’ll land in your inbox next week,


Danny Denhard

Leaders Letter Newsletter

Leaders Letter 189 – This Is Not The Way Book – Unleashing Creativity: An Interview with Author & Founder Andy Reid

Dear leaders, this week I have a special interview with the author of This Is Not The Way, Andy Reid. 

Andy Reid is the founder of Genius Box who help companies big and small address company issues from creating North Stars to creating or optimising company strategies. 

In this interview, I ask Andy 6 questions:

  1. Your new book aka anti-manual “This is not the way” is a mass of knowledge and learnings from your successful career of change making, why an anti-manual and why now?
  2. You have helped many well-known and upcoming companies move their businesses forward, who are the best people to get into the room to create the most effective company-wide strategy?
  3. You interviewed a number of smart strategic operators and facilitators (not just because I was involved) and curated a number of actionable insights. What surprises or new approaches have inspired you to improve your workshops?
  4. You have suggested brainstorming don’t work – what’s the best alternative in getting the best ideas and concepts out of colleagues?
  5. Many companies always problem-solve the same way or mimicking how they’ve always done it – what’s the best way to problem-solve with your decades of experience?
  6. What’s the best piece of wisdom you can share from your anti-manual? 

The Interview

I am also interviewed in the book:

  • I offer my insights around company strategy is baking a better cake
  • How to thrive in workshops 
  • Who to bring into workshops (hint not just the leadership teams but never overload strategy is too many opinions, analysis and time to step out and create the compass is critical). 

Here’s my section

Here’s The Learnings Broken Down

In a world where business books often provide high-level strategies and case studies, Andy Reid’s new book, “This Is Not The Way (The Anti Manual)” takes a refreshing approach rather than the usual approach. 

Andy dives into the motivations behind the book, the importance of innovation, and practical tips for driving creative change within organizations. Andy’s insights and discover how you can become a fantastic creative facilitator alongside several experts interviewed including me.

Why an anti-manual and why now?

Andy recognizes that existing business books often lack actionable tactics for turning strategies into real-world actions. With “This Is Not The Way,” he aims to bridge that gap by providing tools, language, examples, and stories that empower individuals to align and excite their colleagues around a new organizational narrative. This book is a treasure trove of knowledge and learnings from Andy’s successful career as a change-maker. Whether you’re looking for inspiration or tactical guidance, “This Is Not The Way” has something for you.

The importance of getting the right people in the room

When creating an effective company-wide strategy, Andy emphasizes the need for individuals willing to embark on a challenging yet rewarding journey. Making change happen requires tearing down old rules, which are often met with resistance. The best strategists and facilitators are storytellers who can flexibly explain the vision and inspire others to follow. It’s also crucial to involve senior leaders who have a line of sight on the business, as their insights are invaluable.

Surprises and new approaches to improve workshops

Andy interviewed several smart strategic operators and facilitators for his book, he discovered that creative techniques have been around for thousands of years. What may seem familiar to him is often new and valuable to others. Incorporating experiments, stories, tools, and techniques into workshops injects novelty and creates tremendous value for the participants. By encouraging everyone to share their thinking and building upon each other’s ideas, workshops become collaborative and productive.

Say goodbye to brainstorming?!?

Brainstorming has long been hailed as a creative technique, but Andy challenges its effectiveness. Our minds often shut down when forced to generate ideas on the spot. Instead, he suggests providing a clear brief and allowing people time to incubate their thoughts. In facilitated sessions, starter thoughts can be shared, and participants can build upon them. By creating an environment that welcomes all ideas without judgment and capturing them consistently, teams can foster better idea generation and capture.

Innovative problem-solving strategies

To solve problems effectively, Andy advocates for injecting 10% of difference and newness into every endeavour. The brief can provide stimuli for thinking differently while changing the environment can spark imagination. 

An example Andy shares is using a musical metaphor for a project called “Project Allegro,” which allowed the team to design activities and tools that connected to the client’s need for a new perspective. The key is to embrace new approaches and avoid striving for perfection, as progress is often more valuable.

The wisdom within the “Anti Manual”

Through his interviews with various professionals, one consistent message emerged for Andy – the importance of providing a safe space for people to share their thoughts and ideas. Creating an environment of psychological safety encourages individuals to be themselves and embrace their unique styles. 

Stories play a significant role in conveying information and inspiring change. By valuing safety, personal style, and storytelling, leaders can pave the way for a new creative era.

This Is Not The Way Conclusion:

Andy’s book, “This Is Not The Way: The Anti Manual,” is more than just another business guide. It’s a call to action, challenging the traditional approach to organizational change and encouraging individuals to become fantastic creative facilitators. 

By implementing the practical tips and insights shared in this interview, you can unlock your creative potential and drive real change within your organization. Embrace the power of innovation, storytelling, and collaboration, and let your creativity flourish.

This week focus on moving your business forward by learning to do things differently, and refresh your strategy by embracing another approach. 

I highly recommend the anti-manual for executive teams. 

Have a great week and I will land in your inbox next week, 


Danny Denhard

More Essential Reading For Leaders

Leaders Letter Newsletter

Leaders Letter 188 – How To Get Better At Problem-Solving & Develop Leadership Level Problem Solvers

Dear leaders, do you want to know how to get better at solving problems? 

If the answer is no I’d be very surprised. 

When you’re faced with a huge problem or a brand new problem you’ve never faced before. 

What do you do?

  • Do you automatically stress and panic? 
  • Do you look for help?
  • Do you go into autopilot and make quick muscle memory-driven decisions? 
  • Do you revisit or review prior issues and problems to reignite the problem-solving muscle you have been building your whole professional career? 

Reflex Actions? 

We all have a bank of problems we have experienced or been connected to, some learn from them, others struggle to remember the details and don’t have the sixth sense that waves the big red flags in front of us to warn us. 

Problems become a reflex action for many experienced leaders (most don’t even have to think, they act).  

The best learn from problems and develop a sixth sense of how to think and tackle major problems and the most efficient stay calm under pressure, some even thrive. 

You’ll likely have a (unknown) two-by-two matrix in your head of where the problem fell and how you had to tackle these problems. 

The 2×2 could be problem size by problem impact, scored by small to big and then apply the actions right away. 

Reaction & The Ripple Effect Is Everything 

One of the biggest signs of a leader on their journey is instant stress and panic. 

You can always witness a less experienced leader who will run around, make a lot of noise and make people around them feel pressure and stress – this is either deliberate or often a sign they haven’t been in situations before or learnt from related problems. This ripples through the business and causes panic – this is not an environment to thrive in. 

If some appear to thrive in causing more confusion and chaos they aren’t a leader at all. 

Clarify, Remove Confusion, Confront 

The best leaders often will take a beat, ask clarifying questions, review their experience and bring in the best people to solve the problem(s) at hand. 

As I have shared before and in my superpowers and kryptonite newsletter, one of the powers I was made aware of was my “ability not to panic and to be a calm person in business problems” So below is how I got here and how you can apply a similar approach. 

I am often asked in coaching and inside of my problem-solving workshops how businesses can get better at decision-making and problem-solving and my answer is simple. 

Enter The Problem Wiki  

Create an open wiki of problems, and the solutions used and then revisit to remind yourselves you have faced numerous issues before and review how you’d tackle the issue today. 

Remember: Over the last decade (and specifically the last 4 years) we have lived and operated in numerous huge problems and the likelihood is you made 70% good to great decisions. 

In some cases, you may have made quick and less well-thought-through or informed decisions that (may) negatively impact you or the company. If it’s under 10% you’re likely doing a good job. 

The trick is to know – hindsight is a wonderful thing and to add notes to say this was in play or this wasn’t. Remember those guardrails I talk about often, this is where your guardrails will be important to keep note of and understand how to move when required and how to incorporate them in the future. 

Templated Help

The decision document (my free template for sharing the most important decisions and how you got to them and how to ask clarifying questions) is just one way to be able to review your decisions of the last year(s) and then revisit how well you did and where you can optimise decisions for the future. 

Without sharing with your leadership and management team and importantly reviewing how are you going to move forward as a business and let it positively spread throughout your business? Async coaching is something many do not talk about but can be priceless with the right approach. 

This week’s action item for you is to book a slot in your calendar to create a decision document and a problem wiki, review the last big 5-10 decisions and revisit the most important problems and the actions you took over the last year and add real detailed commentary to what, why, who and how you tackled these problems. If you then open this up and share internally you will offer a chance for those around you to learn and grow out the problem-solving muscle. 

Have a great week and I’ll land in your inbox next Monday morning with an extra special leaders letters. 


Danny Denhard

Leaders Letter Newsletter

Leaders Letter 187 – The 2024 Corporate Buzzword Bingo Card

Dear leaders, what are the buzzwords you hate being said every day in meetings, used around the office, on Slack or Teams and stuffed into your emails? 

I bet I have them for you in the 2024 update to my annual buzzword bingo card. 

It’s a playful and the most popular post every year. Over the last two years, both 2022 and 2023 have been the most searched on social for and shared posts on the Focus Blog

The 2024 Corporate Buzzword Bingo Card

What Is In and What Is Out

  • Authentic – most likely the phrase you will have heard from Marketing, then across LinkedIn and now has become a mainstay across the board and senior leadership and becoming commonplace across the business 
  • Convictions – A word many use to justify decisions and insert into speeches and all company emails. Expect convictions to be used thousands of times by the CEO/founder and across the business (likely in connection to the vision and mission being refreshed and to try and inspire when the first performance dip of 2024)
  • Return to the office – mandate — mandate was the most hated work last year and it won’t go away this year. Expect ‘mandate’ to be used in other situations and 
  • Economic Headwinds – despite everyone going to experience headwinds, I expect the phase to be replaced and removed from most boardrooms 
  • RTO – RTO went out as the mandates came in and as discussed in last week’s newsletter the battle for hybrid and mandate is heating up 
  • Microeconomics – micro is out, macro stays, expect microeconomics is to be said less and referenced less and bigger themes replace it 

An important note between the humour, and buzzwords often alienates those who don’t understand them or aren’t taken through the significance of these buzzwords, as a leader you should help your team members understand the importance and consider providing them a chance to use where they are applicable. 

This week’s focus action is to share across your leadership team and have a bit of fun with these and maybe have a laugh at who uses the most, even circle back to them when you are under the bonnet. 

Have a great week and I’ll see you next week. 


Danny Denhard