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Leaders Letter 169 – Leadership Lessons & 5 Questions With Industry Leader & Coach Joe Scarboro

Dear leaders, this week I have a leader joining us who I can only describe as the nicest and smartest leader I have had the pleasure to get to know and have enjoyed a number of coffees with. 

Joe has worked across the C-Suite (holding both COO & CFO roles), been a successful founder who sold his company, led many others and now is coaching other C-Suite leaders. 

This week’s 5 questions are packed full of gems from Joe and I know you’ll get huge value from this.

Connect with Joe On LinkedIn

Joe Scarboro 5 Questions 

Q1/ You have a unique background where you’ve been a leader across the full spectrum, from Chair, COO, CFO and including being a founder. What are the three main leadership lessons you learned from operating across the C-suite? 

Broadly, these sit within the huge topic of “people”.

Having the right people on board is vital – whether that’s the one Co-Founder that you start with or your employees, board or management as you grow. It’s closely linked with purpose, as your values and how you recruit will define your people. Making people mistakes is costly though and this is amplified in the early stages and also when making senior hires at most stages. The downsides are mitigated as you grow, as bad hires have less of an impact, but I’d strongly advise against the temptation to get *someone* in a role sooner, rather than the right person in the role a little later. This is particularly common after a fundraise and during a stage of rapid growth. Creating a robust and well thought out hiring process will serve you well here.

The next tip would be on self awareness. As a leader, you need to be able understand your biases and tendencies in order to make better decisions. For example, acknowledging that you’re bad at delegation because “That’s not how I would do it” (and that makes you uncomfortable) allows you to begin to accept that someone else might not do it the same way, but will still likely get it done (caveated with the above of hiring the right people!). Self awareness needs constant attention though, it’s much easier said than done!

Lastly, I’d go with understanding when to listen to customers and when not to. There are a huge number of examples of successful companies on both sides of that argument, so it’s not as if one way is right and the other isn’t. Understanding how customers interact with your product or service and how they feel about it is generally always important, but if you’re doing something new (be that a totally new product concept, or a new feature) you may be better served by starting with your vision, with a clearly defined purpose for it and working from there.

Q2/ You are coaching across the C-suite, what are the current elements of leadership that are coming up in your coaching that could help leaders to improve their own organisations? 

I see systems thinking and second order effects often not always being given the consideration they need. Leaders deal with a number of issues at the same time, often under a lot of pressure and they operate to solve those issues quickly and effectively. In doing so, they can easily miss fully considering the impact of those decisions on a variety of other areas of their business and beyond. 

A classic challenge of this type is formulating sales comp. Solving for maximisation of incentive (and therefore sales) may seem the right way to go, but there are a lot of other considerations. 

  • What will the impact be on the non-sales team? 
  • Do you make it confidential so as to minimise the impact? 
  • Does making it confidential align with company values? 
  • Will it erode trust within the non-sales team? 
  • Are there mitigating measures you can put in place? 

If you make it transparent, how do you otherwise incentivise the non-sales team members? Of course, you can disappear into this type of thinking and emerge with a huge number of variables and no answers, so the key is to go to an appropriate level of depth for each decision. Having an appropriate heuristic for assessing decisions in this way really helps here, be that something simple like the important/urgent matrix, or something more specialised to the business.

Q3/ You recently took over hosting dinners for Tom Blomfield (the Monzo founder & GoCardless co-founder) from Series A to Series C, are there any themes that are coming that would help leaders understand how to handle today’s demands? 

The startup investing landscape has changed more so in the last twelve months than in the last decade. With the exception of certain areas (AI etc) attitudes to risk have changed, “available funds” are much less available and there’s a push towards profitability that just hasn’t existed for a long time.

This has fundamentally changed most businesses’ strategies. In some cases what was a 5+ year path to profitability now needs to be on a 2 year trajectory because there’s no guarantee that growth funds will be available.

That’s a lot of change to deal with in a short space of time. It’s given rise to a number of themes around hiring, product pricing, unit economics and a lot more besides. Whilst these attitudes are likely to change again, it’s not looking to be any time soon, so these are big issues that need strong consideration from founders and boards.

Q4/ Apart from the mass move to AI, are there any other important moves that you feel all companies will be making in the future? 

I find it hard to apply generic thinking to companies, as every one I have worked in has been different, you need to dig into the nuance and context in order to be able to provide appropriate advice. AI for example, should *everyone* be implementing AI? No. I don’t believe they should. Should everyone be looking at how it impacts their business? Absolutely, but that also goes for a number of areas. It’s more about remembering to lift your head up and consider the fundamentals and macro environment rather than being swept along by the latest hype or making specific moves because “everyone else” is.

One trend that I hope I see come in, is the removal of shareholder value being the de facto, priority number one of a company. There’s already a groundswell of companies changing their charters or otherwise operating with a wider pool of considerations, but I believe we’ll see an expansion of statutory reporting to encompass an element of this too. It’s been happening for years already (see corporate ESG reporting), but I believe there’s a strong chance this thinking will be brought into other areas of legislation too (employment law, consumer protection etc).

Q5/ What was your favourite leadership moment of your career?

There have been many, but most involve helping people. 

As a leadership team in one of my companies, we felt a particular employee wasn’t learning and growing to their potential, but we had no resources internally to help. We were a small company and whilst they were junior in their position, there was no one with more experience than them. We approached them and suggested it was time they moved to a different company, they resisted, but we pushed them forward (and out!). We believed that we were doing the right thing and thankfully we turned out to be right. The employee left, had no trouble finding a new role (including a 50% salary increase) and their career has since taken off!

This was packed full of insight and actionable tips, I am sure you will have a lot to think about this week.

So this week’s focus item is to re-read Joe’s brilliant answers and see where you can apply his lessons. 

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

Thanks, 

Danny Denhard

Read the other 5 questions about leadership interviews