How do you keep developing as a leader?



Are you doing a good job? Do you know what skills you need in your role and whether you have them or not? Do you know what best practice looks like?


An employee can usually expect to receive feedback from managers or colleagues which they can use to help them develop. Though the feedback can vary significantly in quality, frequency and usefulness, it is a key tool used by companies to help people understand what is expected of them at work, where they are doing well and where they need to focus their development efforts to improve or get to the next level.


Feedback is usually based on a reasonable to good common understanding among your colleagues of what skills – whether technical skills or soft skills - are expected in your role and what good looks like for that role in a company of the size you work in. This understanding may or may not be supported by a competency or development framework, where this is detailed.


But what about CEOs, founders, or leaders of functions? In these roles, the need to understand what good looks like and what skills one might need to develop or hone is arguably the most important – you are more likely to be the only one who can do your role in the company and your ability to do the job can mean the difference between success and failure of a whole company. How do you develop and get honest high quality feedback when, by the nature of your role, no one else in the company has previously done your job?


We decided to swap notes, to see what we could learn from each other.


Main takeaways from our discussion:


“Not all readers are leaders, but all leaders are readers.” – President Harry S. Truman

1. Creating time – to read, think, ask advice, consult a coach, reflect - is the number one thing you can do to develop as a leader. Being too busy is the number one barrier. Listening to podcasts/audiobooks while driving, exercising or walking the dog is possible. But if you find yourself with no time to reflect and read, you need to take a serious look at your schedule (this will be the subject of a future WITSEND zoom)


2. The same questions apply to leaders as to others - what is required of me, what does good look like, where do I need to develop? - you just have to figure out a lot more of this for yourself


3. Top sources of feedback and development at senior level were broadly agreed


Very strong focus on self-reflection and learning from other leaders

  • Podcasts, books, TED talks and articles (see separate blog post for recommendations) to stimulate ideas and questions were mentioned by almost every leader in the discussion

  • Talking to other CEOs / founders / peers doing a similar role in other companies / mentors with CEO experience – either generally about what they do that works or about specific issues, to get their insight - was also seen as very powerful; building a network that enables you to have these conversations is helpful. Happily, most people had found that others in similar roles were usually happy to exchange notes (at WITSEND we try to facilitate exactly this!)

  • Watching others lead (eg by doing Board roles, consulting assignments or building long term relationships with leaders from other companies, where you can discuss and hear the outcome of different situations over time) then adapting what you like that they do to your own style was also cited as a way to learn

More than half of the leaders/founders/investors we heard from have had a coach in their current role

  • Preference was stated for coaches that can collect 360 degree feedback (including from the Board) and tell it like it is – “super honest, not trying to please you”

  • Important to get recommendations. Given so many coaches out there – it’s hard to pick a good one without recommendations from people in similar roles (I will publish a list of coaches on witsend.online recommended specifically by this group, plus what they are particularly good at)

  • Preference stated by some for a coach that has senior executive experience and has coached other CEOs and really understands the role and its challenges

  • Some people have found it helpful to get a coach for the first 100 days when stepping up into a new role to make sure they get the mindset shift you need and go in thoughtfully and deliberately

Feedback from teams was generally on the list but not at the top of the list for most CEOs, founders and investors

  • As in most roles, it can be a challenge to get honest feedback or insights beyond your management skills from direct reports. However, engagement surveys or feedback on what’s working and what’s not in the company / team can be useful as it is easier for people to be honest in these situations and, as a leader, it’s your behaviour or behaviour you allow that creates the culture

  • Mentoring more junior people in your company is also a great way to build relationships and, over time, get more honest feedback about how your leadership is perceived

Feedback from Board members was barely mentioned in the top sources

  • Not clear why (might be something to dig into another time). Quite possibly individual Board members are seen as mentors, rather than being asked for “feedback” in the traditional sense

4. Managing through tough times is one of the best ways for leaders to develop, stressful though it is. This forces you get out of your comfort zone and try new things


5. Reflecting on your values and what sort of CEO you want to be / what sort of culture you want to lead is important to allow you to filter all the advice you receive and work out what you want to try - you can't do everything


“Creating time is the number one thing you can do to develop as a leader. Being too busy is the number one barrier” - Kathy Harvey, Associate Dean, Saïd Business School, Oxford University