Anonymous Career Advice

How To Connect Company & Company Leadership Team

In this week’s anonymous career advice column, we hear from someone who is facing common struggles many of us do. 

Dear focus, many of the company is struggling with connecting with their bosses and the ELT. They are disconnected and really wrestle with being approachable and being able to commit to the direction we are going. Any tips?

Thanks for sharing your experience today. I will take a guess this has happened for a prolonged period of time and likely started before the forced work-from-home experiment. 

There are five givens within businesses who are going through a phase of change, it sounds like you are experiencing three: 

Anonymous Career Advice

Is it possible to have a non subject expert as a department lead?

This week’s anonymous career advice centre’s around a common issue where the department lead is not a subject matter expert and struggles with driving their own teams forward.

Dear focus, my department lead (my direct boss) is not a subject matter expert. They struggle with having the right level of in-depth conversation with the team and it’s impacting our department and delivering important products.
What would you recommend? 

This is more common than you believe and something many of the readers will be questioning or have questioned recently. 

There are often a number of ways to look at this and typically falls into two sides or two schools of thought. 

The Two Sides 

Anonymous Career Advice

How To Reduce The Work Life Blur?

This week’s anonymous career advice comes from a manager that is looking to help their department in reducing the blur between work and home life, especially with many businesses now operating in the hybrid model

Dear Focus, What are the five things you would recommend to help my team reducing the work and life blur?

This is actually something many managers just are not thinking about and I want to thank you for stepping up and asking this question. 

There are much bigger methods in tackling this but requires a fair-sized budget shift and significant change from your team members, however, here are my five simple but ultimately actionable recommendations:

Adding work boundaries helps to guide teams to work to core hours and not react to each request out of work hours

1: Add Boundaries

Ensure you set the right level of boundaries for your teams: 

  • Whether that’s their workday or out of hours
  • The teaming knowing it is ok to not have to reply to slack, teams or emails out of hours
  • Your boss emailing you outside of working hours does not need a reply 
  • Some teams will have to work out of hours, this does not mean the company does and knowing that you will receive 

I have worked for companies that operate across multiple time zones and setting the expectations that your time zone is when you work and respond is important.

Likewise, if you are a senior leader or executive, you work different hours to the rest of the business set the example and allow teams to know you do not expect the same and do not want them to blur the line. 

Remember sending an email or instant message is only ever convenient to the sender, rarely ever to the receiver.

Having worked agency-side and ran agency business operations, it is important for you set the precedent at your agency that working hours and delivering on deadlines happens within work hours.
This will be a huge selling point for your agency and operationally savvy agencies tend to outperform less operational smart agencies. 

Having official works apps and software helps to guide teams around what is work and what is not
Anonymous Career Advice

How To Win At Hybrid Office Politics?

Today’s anonymous career advice is around the upcoming issue many are going to encounter, hybrid office politics, concern over conversations that happen in person or was had in person while you are working remotely or from home and impact you, your department or the direction of an important project.  

Dear Focus,
I’m struggling with the ongoing leadership politics and the political shifts while working hybird, how do I keep up and stay on top? 

This is going to be an important lesson for many professionals to understand and decide how they tackle the new political battle. 

Something to remember, being political is always an option, there are many executives who can operate without being consumed and they concentrate on their teams delivery. 

With that said, unfortunately, (PQ) Political intelligence is usually a vital skill many do not develop and keep on top of the political pulse within their business. 

Some businesses are built on politics, it’s how it operates and likely was bred into the management subculture. 

A thought process to go through, can you reduce the demand for you to get involved? 

Anonymous Career Advice

Designing The Ideal Management Team

This week’s anonymous career advice is connected to organisational design and scaling businesses in the right way. I break down five essential roles to be successful with.

Dear focus
We are struggling to build our leadership team, we are growing and it’s time to mature, what does the ideal management team look like? 

Management teams and leadership teams are unique to every business.

Every business requires something a little different, from the way you are created, the people you included and then those you invite regularly to the team you rely upon to make the most important decisions in the growth and in some cases the survival of your company. 

When designing your organisation, team design is difficult, department design has more complexities, the management team is typically seen as the easiest part as you invite the most senior around the table. I believe this is where many companies get this wrong, your management team should be those who excel at their jobs and take the extra responsibilities on and “play their role” and something that is constantly overlooked destressing the business. 

Here are the roles I believe you should have on your leadership team: 

Anonymous Career Advice

Should Every Team Have A Roadmap?

This week’s anonymous career advice is a good question asking should every team have their own roadmap?

This is an important question around being transparent, collaborating and being a collective in changing and adapting how you work for the success of the company.

Q: Dear focus, should every team actually have a roadmap?
And should we connect to the company roadmap?

This is a great question! 

I talk about this topic a lot and the process of creating a roadmap for most teams is something I am a fan of.
Anything that actually moves teams away from a finger in the air Gantt Charts is a step in the right direction and takes a list of work and turns it into more deliberate work. 

In the recent strategy articles, I suggested in WTF is strategy and why strategy is often misunderstood for tactics, strategy is the overarching plan of action for the whole company to get behind and work inside of.
Strategy is the important guide for your company, adding in the successful boundary lines. Roadmaps are the same.

Like strategy, a roadmap has to be clearly defined and understood, there should be no misunderstanding of what a roadmap is and is not, what it includes and why these important items are included.

Like strategy, the activity of planning and reviewing is about what you are not going to do and why these handful of items made the cut onto the roadmap. 

Typical product roadmaps need improving but helping to guide new teams will be essential to helping your business to succeed
Anonymous Career Advice

Google Manifesto It’s Ok To

This week’s anonymous career advice centre’s around Google’s Manifesto which has been shared far and wide praising their approach to working from home or working remotely. It’s important businesses consider the influence Google have and the internal PR machine behind this before creating their own manifesto.

Dear Focus, Google’s manifesto has been all over LinkedIn and my team have asked me why we don’t have one? What’s the best way forward? 

Google are in a place where they can share internal best practices and it will always be shared and leak externally. 

This is often something that just happens, something to consider is how much of this is true and how much of their internal manifesto actually happens and is accepted. 

Anonymous Career Advice hybrid office

How To Stay Visible When Working Remotely?

Dear Focus, how do I stay visible when working remotely? 

Working remotely or in some cases hybrid has become a challenge for some team members to appear to be visible. 

It is actually a series of different questions I have received via the anonymous career advice form in recent weeks. 

As recommended in is playing the game essential advice article, there are many times you will need to be available, be part of things you do not naturally lean toward, times where what you need to do is be more proactively and importantly managers, bring those up around you. 

Delivery Presence, Deadlines, Internal Networking are the key categories for you to consider when considering how you are visible, and importantly, how you might manage and tackle this as a leader of the team.


  • Delivering on a project, a campaign or a product release is the best way of staying visible, being able to take your opportunity is always the best way of staying visible and demonstrating you were part of important part of work. 
  • Be The Sender: Sending out the message that you or your team have delivered on a large project or campaign is a great way to be seen and a way to be celebrated or supported. 
  • Be part of fixing the problems. One problem two solutions is a great framework to use and introduce
  • Celebrating the metrics vs just celebrating delivering is always favoured within mature businesses so keeping this in mind is impartive.
  • If you and your manager are not having regular check-ins but you would like to ensure they know what you are ‘doing, done and achieved’ I recommend a weekly email to your manager with (a) what is working, (b) what are you working on and (c) what has been delivered and (d) anything to be cautious of, trends within the industry or larger themes you should be on top of.  
  • Managers: Be able to congratulate and bring your team members to present and send the email or company-wide slack update is essential. If you are a c-suite exec or on the management team always bring your team members to discuss the delivery and early numbers in leadership meetings, help to prep them and bring them along the journey 


  • Build out your presence while online meeting, offer to take notes, chair the meeting or own the workstream. This is more work, however, with structure and operational excellence this will help to stay visible and build your presence around the company 
  • Concentrate in the meetings and taking part of meetings, always be prepared to add value or unique insights (versus adding more opinions) and contribute to the follow-up conversations or offer to lead new projects.  
  • Managers: Asking for your team feedback and for someone’s expert opinion particularly when they prefer to be asked is essential, it will help you bring on others presence and their visibility but also helps the team to know their presence and their expertise is vital for the companies success. 


  • Something many have allowed to slip while working remotely is deadlines slipping or not hitting deadlines.
    Hitting deadlines will always be essential and be vital for a companies success. Hitting a deadline is often the difference between being seen, respected and having positive mindshare vs having negative mindshare and having trust.
  • If/when possible create the GANTT or the roadmap and be the point of contact on the deadlines and deliverables 
  • Be deliberate in communications, not over-communicating, update colleagues on the progress of the project and how you are progressing against deadlines. On many occasions, this is happening however remember internally marketing is as important as externally marketing and applies to projects of all sizes 
  • Managers: Setting realistic deadlines – this is the flip side when a manager of a team or business leader, very often setting aggressive deadlines actually hinders your teams chance of being visible and hitting targets and creating a negative 

Developing Your Internal Network 

  • Build out connections – something when working remotely or in the hybrid workforce is you tend to neglect networking and building internal and external connections, actively work on networking and connecting with colleagues within the organisation and have quick coffees and be available to help colleagues if they need someone to assist them or be a support network  
  • One to one’s are always important – ensure you are keeping up with your one to ones, where possible look to meet with your bosses boss in skip meetings. This is often invaluable and creating a connection with your bosses boss or your team’s team creates better connections 
  • Virtual lunches – this might sound like more work and your time however one of the missing parts of connections when remote or hybrid is eating together and drinking together. I recommend making the same lunch and having 30 minutes where you just talk or connect over something trivial, a tool like donut (slack tool) will help you with virtual meetings and randomised meetings, you scheduling this and working with colleagues will be important 
    Here are a number of hybrid work tools and apps to help you become successful in hybrid.  
  • Hybird lunches – sometimes teams go to lunch when in the office and those who are not there will miss out, where possible consider how you might integrate those working remotely or organise a day and time where colleagues can come together and eat or allow those remote to be present in the hybrid lunch. This also works offsite too. 
  • Network events – something a handful of mart companies have created is hybrid and remote network events with tools like hopin and riverside and connect colleagues in break out rooms, with Q&A between departments and presentations on important projects and successful campaigns and releases 
  • Managers consider building out management pods to connect you and your management team more closely 
  • Managers: It is important to remember remote offsites and remote sessions are not always the silver bullet to bring teams together 

There are many more brilliant pieces of advice for managers and leaders in the fixing the broken world of work podcast

Best of luck and keep moving forward.


Danny Denhard

Read the future of work keynote from the end of June to learn more about how the world of work is changing and how to be successful in the hybrid future.

Anonymous Career Advice

Leadership Team Issues

This week’s anonymous leadership advice comes from a new leadership team member who is struggling with the purpose of the leadership team and their role on the leadership team:

Dear Focus, It’s the first leadership team I have sat on and I’m struggling to work out the dynamics and what’s important. There’s a lot of talking and not much action. What should I do? 

Management teams can be hard work. They can be exhausting. 

S-Teams can seem daunting, they can seem aggressive, typically passive-aggressive and create an atmosphere where many appear not to like each other personally or professionally. 

It is rare these are friendly but asking difficult questions are essential to make progress. 

Many start out with good intentions, unfortunately, many turns into environments some thrive and others struggle with. 

This is where game playing has a huge step change and understanding the rules of this game is critical to your success. 

Something to keep in mind in your situation is what function are the meetings serving and what function am I serving on this leadership team? 

It is important to remember most Management Teams are particularly bad at onboarding their colleagues on the leadership team and worse at explaining the what, the why and the how.  

The essential factor in MT’s or ELT’s is not to condition those around and below you to copy your behaviours and roll out this into the company wide culture.

Management Team Buddy

One important lesson I learnt and recommend to businesses of any size is to create a buddy system with someone else you trust on the leadership team and build upon that relationship and understand the unique set of rules you have in your meetings and understand how you add value to the meetings and to the company as a whole. 

Understanding the unique dynamics and the HiPPO rules will be important milestones for you to set out and understand. 

New Management Team Member Guidance

In your role as the newest member of the LT or ELT is holding your colleagues accountable and ensuring the business delivers guidance and keeps ahead strategically. 

This can often be lost in the noise and the routine that management team meetings can become. 

Tip To Keep Front Of Mind

One tip you will struggle to find elsewhere is to remember not to become too defensive or protective of your team or business line and allow the numbers to do the talking and introduce your team members to present their numbers, their feedback or ideas to the group where possible. 

Over Indexed Voices

Something I have observed on different leadership teams is if you are a sales-driven business, you will over-index too much into the sales team voice without balance.  

if you are a product based company (driven by product direction and usage) you can lean into the product teams vision and “their strategy” too much without hearing from valuable partners like Marketing or customer service and success. It is important to keep on top of this and ask for more input from those partners.

If the CFO / FD or CEO / MD speaks too much, you will be part of a HiPPO driven business and this will cause numerous friction points within the leadership team. 

I recommend reading is it time for management pods article. 

What is important to ask your colleagues: 

  • What are your management meetings for? 
  • Who controls and holds colleagues accountable? 
  • Why are you meeting in this cadence? 
  • Why do we meet for this length of time? Can we optimise this process? 
  • What function are you all serving? 
  • What role do I serve on this leadership team? 
  • How do we inform our colleagues and teams of upcoming projects and campaigns? 

Once you either ask your colleague and answer or undercover and answer the quicker you will feel part of the management team and the closer you will get to adding value. 

Good luck on your leadership team journey. 

Danny Denhard 

If you are in need of management team training or executive coaching or need a professional mentor get in touch below:

Important Leadership Resources:

The Hybrid Work Guide

The top 20 good managers vs the 25 bad manager examples

5 leadership books to read in 2021

Business lesson from Jeff Bezos

Elon Musk’s Business Rules

How to fix bad company culture

Taking over from a bad manager

Do yave your own question you would like answered?

Anonymous Career Advice

Anonymous Career Advice – Company Breaking Apart?

This week’s career advice is also business advice.

The Big Question: Is My Company Breaking Apart?

Dear Focus, there are a number of people leaving my company, we used to be so close, how can I keep my colleagues with me and complete our mission? 
— “Anon” Startup Founder  

This is common in every business, regardless of size, people leave businesses for many different reasons, one of the main reasons is career progress, the other main reason is the company has changed or changing in a direction staff just don’t align to. 

The Great Resignation?

We are about to see what some people are referencing as ‘the great resignation’ is a large number of talent will be looking to refresh their roles and change roles for career progression. 

You are likely experiencing some of this and then a blend of a changing culture.

Communications Is King, Queen & Everything Inbetween

As a startup founder, you were likely close to the team and then had to move away or actively decided to distance yourself from the team or departments. 

Being deliberate in this step was important however with focused comms around this move this can cause friction and disconnection. 

Questions to ask yourself:  

  • Are there patterns happening? 
  • Are there key internal influencers who have left the business? 
  • Has our company culture taken a hit with the change? 
  • Were we too close? 
  • When working remotely did teams drift apart? 
  • Have we brought in a new layer of management recently?
  • Is performance suffering? 
  • What motivates my current team? 
  • Is there data to show that staff are hitting the time-based limit? 
  • Are exit interviews highlighting any outliers? 
  • Which was the biggest change you made and how long before staff left? 
  • Am I struggling to hire? 

If there are patterns and data suggesting there were some steps that might have created disconnection, ask yourself are you moving forward as a business and are you creating something people will want to join in the short term and in the long term. If yes, this might be a business phase you fight through some of the growing pains. 

Business growth can be hard and many times has to be seen as a marathon, not a sprint. 

Team Not Family

Although this came under question, the CEO of Shopify Tobias Lütke suggested that your business is a team, not a family. It is likely time you consider the internal framing of your business and understand that a team comparison is far more representative than a family. Despite it might feeling like a dysfunctional family, families particularly in the startup space create connections when broken are too hard to rebuild or readdress. 

Shopify Email Quote
“Shopify, like any other for-profit company, is not a family,” “The very idea is preposterous. You are born into a family. You never choose it, and they can’t un-family you. It should be massively obvious that Shopify is not a family but I see people, even leaders, casually use terms like ‘Shopifam’ which will cause the members of our teams (especially junior ones that have never worked anywhere else) to get the wrong impression.”

“The dangers of ‘family thinking’ are that it becomes incredibly hard to let poor performers go. Shopify is a team, not a family,”

Learn From Success Startup Leaders

Remember businesses that are close have to have agreed leadership principles, one important tip to borrow from Whitney Wolfe Herd CEO at Bumble, is that you are making the decisions for the best of the business and if you are friends this should not hinder your judgement and actually be best for the business. 

Good luck and remember even the best and top talent leave the biggest and well-paying companies. 

It is how you react and lead in creating the best business for your customers, shareholders and importantly for your current teams and talent coming into your business.

Danny Denhard 

My Personal Recommended Reads: