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A 360 review for startup CEOs is an underutilised tool that can relieve internalised pressure, while offering a path forward towards more peace and better performance.
In this essay I’ll talk about 360 reviews for startup CEOs, which are a process of getting feedback from key colleagues in order to help the CEO grow personally and professionally through better self-awareness.
A CEO I used to work with, let’s call him Oscar, told me that he hesitated to start working with a coach because he thought a coach would put more pressure on him to perform better, and he was already under more than enough pressure from his own inner critic.
Pretty much every single CEO I did a 360 report for was at least a bit nervous about how hard it would be to read about all the “bad stuff” that would be in that report.
I understand the sentiment well because when I was a startup CEO myself, I felt an incredible amount of internalised pressure. It feels like an inner voice telling some version of “if you don’t do this or that, you’re failing, so go and do it now” story.
It’s genuinely rare to come across a startup CEO who doesn’t feel this pressure inside, and if they don’t, it’s almost inevitably because they worked on integrating their inner critic into the rest of their psyche.
Paradoxically, and counter-intuitively, it is the inner critic that’s working hard from building a better relationship with it. An inner critic might say, “You’re not working hard enough, even though you’re exhausted, and if you tell anyone about it, they’ll make you even more exhausted by making you work harder, which you know you should be doing anyway, so don’t do it”. It’s irrational, but that’s how our inner critics usually are.
In practice, doing a 360 review of a CEO’s performance is never about putting extra pressure on them. More often than not, it paints a more positive picture than what the CEO is probably imagining in their head.
If I were to generalise, many startup CEOs imagine that they are doing a worse job than they are actually doing, which leads to their inner critic putting a lot of pressure on them. This, in turn, might prevent them from actually making changes, because they mistakenly believe that better performance comes through even more pressure, which they wouldn’t be able handle.
In fact, a 360 review process is meant to give a more accurate picture of the CEO’s performance and offer a way forward, which is never through more pressure, but through a clearer understanding of their strengths and weaknesses.
How does a 360 process work?
Any 360 process starts with discussing the goals with the CEO and selecting key participants, usually their entire senior team and some or all of their board members, plus possibly other key people in the organisation. The goals can be broad, such as understanding how others experience working with the CEO, or narrow, e.g. understanding why the CEO might be struggling with a particular aspect of their role.
There are, broadly, two ways to approach it. One is to send the same questionnaire to everyone, including the CEO, and then reflect on the results. The advantage is that everyone answers the same questions and it’s vastly faster and cheaper than individual interviews. This gives a lot of quantitative data: ratings and numbers. This can be a good approach if the entire senior team is going through a 360 process at the same time.
The other approach is interviewing every participant, aiming to cover all the key areas, but also being open to what’s said between the lines or not said at all. This is time-consuming and more expensive, but gives much richer qualitative data.
Then, the results of the interviews (or surveys) are compiled into a 360 report that is debriefed with a CEO with two goals in mind. One is to really think it through and internalise. The other is to translate it into a personalised, actionable development plan.
My own 360 review process
Every coach has their own approach to doing 360 reviews, guided by their experience and philosophy. The coach isn’t a passive administrator of a test. Instead, they play an active role actively choosing what parts of the feedback (and there will be a lot!) to pay attention to, what to ignore and how to interpret the results.
I do qualitative 360 reviews, interviewing every participant for at least 30 minutes, transcribing the conversations and then teasing out themes and connecting the dots from all interviews at once as I prepare a 360 report to debrief with the CEO.
I love to include quotes from the participants, but I always ask for their permission, which not everyone is comfortable with. I’m fine with that: I’d rather see everyone being completely open during the interviews, knowing they won’t be quoted.
I produce two versions of the report: one with quotes from the participants, which is meant for the CEO’s eyes only, and one without, which the CEO may or may not choose to share with all participants.
The report highlights a few areas of strength and a few opportunities for growth, together with a few recommendations for the CEO. It’s important to discuss both strengths and weaknesses, because if we aren’t fully aware of our strengths, we may be under-utilising them.
I usually gently suggest sharing the report with the participants because it can be a very powerful step to show the team what themes came up and what lessons the CEO is taking from it. It’s an opportunity to role model openness to feedback, vulnerability and growth mindset to the team.
When the report is ready, I discuss the findings with the CEO, usually during more than one coaching session, and we translate it into practical next steps. Over the next few months as we continue working together, we continue to reflect on the lessons from the 360, because real change takes time and consistent effort.
The really interesting bit of the process is not the report itself, but the debrief with the CEO. Often, it’s not that facts that are illuminating (“I know some on the team hesitate to speak up in meetings”), but the reasons behind them (“Oh, that’s how my actions ruin psychological safety, interesting”).
As a coach, I inevitably bring my judgement and experience into the process. For example, being closely involved in a particular area of the business can be the right thing for a CEO to do at an earlier stage of the business, but the very same behaviour becomes a problem as the business grows. Is this particular behaviour a concern for this particular CEO at this particular time?
Or, consider advice that every participant has for the CEO. It’s an invaluable source of insights, but it needs to be seen through the lens of what the startup CEO should be doing at that particular time. Their job isn’t to be liked by others, after all. Furthermore, their job evolves as the startup evolves, as I wrote in this essay:
This approach means that my perspective as a founder and a coach inevitably becomes part of a process. This is how I would want my own 360 review to be done: by someone with an understanding of what it’s like to run a startup who brings their own judgement and perspective into the process.
When is it best to do it?
Given the time and expense of running a 360 process, as well as the time it takes to internalise and implement the changes, I wouldn’t recommend doing it more often than every 1-2 years.
I often recommend it at the beginning of a coaching engagement, but not to all founder CEOs. It depends on the scope and goals of our work: it can really support our work, but it can also be a distraction if the CEO is clear what they need to focus on.
I often think about my work with Oscar, that CEO who was worrying that coaching would put additional pressure on him. As we were wrapping up our engagement, he shared that our work actually took a lot of pressure away from his shoulders. I wasn’t surprised: progress in coaching is made through self-awareness, not pressure. Furthermore, increased self-awareness tends to relieve internalised pressure as we start seeing much better ways to achieve our goals than simply trying harder.
Considering doing a 360 report for yourself as a startup founder? Hit reply and let’s have a conversation.
Startup CEOs in transition peer group
Nearly every startup CEO thinks about stepping down at some point. Yet, almost everyone faces these two questions in solitude, because admitting that you're considering leaving your business is still taboo:
How can I decide to step down?
How do I prepare the transition?
I'm running a peer group of startup CEOs where we explore these questions together, and I’m about to launch another one. This is for you if you are:
A startup CEO trying to decide whether to step down
A startup CEO preparing the transition to a new CEO
Here's how it works:
Meeting bi-weekly for 90 minutes
No advice giving, only sharing experience to see how others are navigating questions that torment us
Strict confidentiality expectations
No more than 5 founders and me as a coach and facilitator
Join and drop off at any point
Monthly fee invoiced discreetly (so that your finance team doesn't know you might be considering stepping down)
If you are interested in joining, drop me a line on firstname.lastname@example.org. And if you know someone who might need this, forward this to them, they'll say thank you.