It feels like coaching as a leadership skill is going out of fashion in some circles. Replaced by the increasingly popular idea that leadership is really about telling incapable people what to do.

I see this in the recent rise of authoritarian leadership in politics and business, in the hubbub of ‘Founder Mode’, and perhaps in a broader and more concerning trend I’m picking up - the growing sense of contempt between founders and their employees.

Of course not all founders and not all employees, but enough to join the dots without too many big leaps. Founders who see their employees as a nuisance getting in the way of ‘real work’ as opposed to an enabler of it. And in an age of AI, the techno-optimists who dream of replacing their employees entirely with compliant AI agents.

I heard an interesting theory recently (I can’t remember where so apologies for lack of credit) - that tools like Slack and Workplace have played an important role in this contempt. They’ve made it easy for employees to speak out, created more direct lines of communication, but all in that frenzied kind of a way that seems inherent to digital communication.

They’ve also played into some leadership anxieties. Founders in a state of vigilance - longing for that warm feeling that everything is going well; that the people around them care; and that all hands are on deck to make things a success - don’t have to trawl for long to find things that feel to them like a waste of time and extrapolate from there. Sometimes this might be a founder looking for problems where none exist, other times the concerns are valid - I recall seeing a lengthy complaint thread about the size the tomatoes were cut to in the Meta salad bar for example!

Despite all this, or even because of it - I believe that coaching as a leadership skill is more important than ever. That even in an age of AI, people will continue to be your greatest asset and coaching will continue to be a means to empower them. That as messy and frustrating as ‘the people stuff’ can be, it’s your role as a Founder to hire the right team and create the conditions for them to do great work. That whilst being directive has its place, if it’s your primary method of leadership then you’ll simply instil a sense of learned helplessness in those around you. The more you direct, the more people will need to be directed.

So I’ll share a few thoughts, dispel a few myths, but the main aim here is to give you some practical stuff to start putting into practice, because frankly, the biggest barrier I see to Founder as Coach is simply that founders aren’t taught how to coach effectively.

What follows is a modified version of the content for a workshop that Sarah Thorpe Scott and I recently ran with Creandum in London. If this feels valuable to you and your team then get in touch.

What I believe coaching is

The word ‘coaching’ is not a regulated term so can (and often is) used to cover a multitude of sins. When I talk about coaching here, I’m talking about a certain mindset and set of leadership behaviours.

The Coaching mindset

As a Coach I believe:

• You have what it takes and are best placed to solve your problems.

• You process the world differently to me. I can’t assume I understand how you think or feel about a particular situation, and I’m genuinely curious about your perspective.

• My role is to support and challenge you, not solve the problems for you or try to get you to do it my way.

• It's not my job to always be the expert.

Coaching behaviours in leadership

• Communicating clear context on the bigger picture e.g. why is this a particularly critical milestone for the company? What’s the strategy that informs this? What are we optimising for here?

• ‘Contracting’ around the relationship - it’s vital for any leader to unpack the implicit assumptions between ‘boss’ and ‘employee’ to ensure transparency and an effective working relationship e.g. I see it as my job to give you the context and the right mix of challenge and support to help you do your best work. What I most need from you is the context to help me do mine, which might include things that are blocking you, opportunities you see to accelerate, and importantly feedback for me…

• Asking questions more than offering advice or proposing solutions - this applies to almost any walk of life - people mostly don’t want your advice, even when they ask for it. Offering advice, particularly unsolicited, undermines the other person. You’re essentially saying I think I know better here. That’s probably not your intention at all but more often than not that’s how it’s going to be processed by the other person.

• Actively listening - that means listening to understand rather than simply to respond. It means listening for meaning, not just words. It means making the other person feel heard, not just hearing what you need. It means listening for the things that aren’t said as much as those that are.

• Getting to the heart of the matter - clients often come to me with a ‘presenting issue’ i.e. a thing that they say is the issue. To name an example from a very recent call - I’m having problems with my board. If I were to jump out of coach mode and into problem solver, I might immediately offer up a bunch of advice around board best practices. But a) they know most of that already; b) they have Google/ChatGPT; and c) most importantly - knowledge of how a board should run isn’t really the problem (or at least it’s only a small part of it). The heart of the matter lies somewhere much deeper. Next time a direct report shares a ‘presenting issue’ you might kick off the conversation with a question like ‘What makes that particularly challenging for you?’

• Showing you care - underlying all of this should be a foundation of trust forged on the basis of you genuinely caring for the other person and seeing them do their best work. Care manifests in lots of ways in leadership - by your words, yes, but also by your actions, however small. If you constantly turn up 5 minutes late for your 1:1 then what you’re communicating is I don’t care enough about you and this conversation to turn up on time.

What coaching is not

The single biggest mistake I see people make is confusing ‘coaching’ with some idea that you have to be soft and lovely all of the time, indirect, or lacking in intensity. Coaching can come with both fire and love. Sometimes you do need to light a fire under someone. You almost always need to say the hard thing. But you can do that without being an asshole.

The second biggest mistake I see is those who try to use coaching as a jedi mind trick to manipulate people into doing what they want whilst having them think it was their idea. Firstly, they’re unlikely to be able to pull it off - the ulterior motives are almost certainly going to be tangible for the other person. Secondly, it’s a bit of a cowardly way out of a more direct conversation that almost always leads to frustration for both parties. Sometimes there are things to be directive about and it’s my belief that you should just call a spade a spade in that situation.

Why coaching is important for founders?

• It’s more scalable - if people depend on you to solve their problems all the time then you become a bottleneck. Highly directive founders almost always run into trouble once the company reaches a certain size and they can no longer stay across all of the detail.

• It allows you to maximise your leverage - there are many ways for a founder to add value within the organisation. Part of the challenge comes in working out the ways in which you can maximise your leverage at any point in time. Being a great coach is a skill that can significantly increase your leverage.

• It’s a more motivating way of being led - so can increase buy-in, velocity and accountability across the team.

• It often leads to better outcomes - problems being solved by those closest to the detail.

• It avoids the learned helplessness that plagues teams that are always told what to do - as stated above, the more you direct people, the more they need to be directed. Good people who can self-motivate and take ownership of big and important stuff will thrive in a more coaching-oriented environment and will walk out the door if that’s not the case.

• It’s a great set of life skills to develop - as a parent, a spouse, a friend - these are skills that will deepen your sense of connection with people that matter to you in any walk of life. One of my favourite moments with clients is when I hear about how their own growth is spilling into their personal lives - how they feel better connected to their kids; or how their spouse commented on positive changes they’re seeing.

When to coach

There’s no simple right answer to this question. Part of being a skilled leader is knowing how to judge the needs of the moment and act accordingly. But here’s one simple mental model you might use to inform the mode of leadership you employ:

Coaching tips

In a workshop or training this might be the moment to pair you up and get you starting to practice some coaching skills. Sadly I’m not there with you so what follows is a set of tips that you might take into your next 1-1.

• Adopt the coaching mindset:

  • You have what it takes and are best placed to solve your problems.

  • You process the world differently to me. I can’t assume I understand how you think or feel about a particular situation, and I’m genuinely curious about your perspective.

  • My role is to support and challenge you, not solve the problems for you or try to get you to do it my way.

  • It's not my job to always be the expert.

• Ask an impactful opening question e.g. ‘What’s the most valuable thing for us to discuss today?’

• Get really curious - imagine that your job is simply to get to a clearer understanding of what’s challenging about this situation for them. Ask questions that align with that goal (see the questions cheat sheet below for some inspiration).

• Keep it simple - long questions get lost in translation. It’s amazing what a simple, ‘And what else?’ or ‘tell me more,’ can do to unlock deeper levels of the conversation.

• Listen to your own intuition - see what your own intuition tells you about what needs to be said or asked. Often your unconscious is doing a better job of processing subtle signals than the rest of you.

• Give the gift of silence - when I first started coaching I used to have a sticky note stuck to my desk with ‘W.A.I.T’ written on it, which stood for ‘Why am I talking?’ Most of us (me included) have an inclination to fill the silence but it’s amazing what opens up when you start to train a new habit. One thing to play around with is a 5 second rule - you can’t say anything until there’s been at least 5 seconds worth of silence. It will feel uncomfortable but give it a try.

• Offer reflections - these shouldn’t be charged judgments but simply things you’re noticing that seem important e.g. ‘I notice every time we discuss X you seem to tense a little. What’s happening for you?’

• Land the plane - keep an eye on time and with 5 or 10 minutes left ask a closing question such as ‘what are your takeaways from this conversation?’ Or ‘what needs to happen now?’

• Make a clear agreement - this may or may not be necessary depending on the context, but you might conclude with ‘what do you need from me to move forward?’ and/or ‘When shall we next discuss it?’

And it can be as simple as that.

Becoming a great coach takes time but a little goes a long way - you don’t have to be a great coach to start coaching and to start feeling the benefits of doing so in how your team responds.

I hope what you’ve read here gives you enough to experiment with for now.

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