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Lonely at the Top

Writer's picture: Matthew DaviesMatthew Davies

Updated: Jan 23

This week, more through luck than planning, I've had the pleasure of speaking to a number of CEOs of small and medium sized businesses. The variety in my work is something I've talked about before and, along with the flexibility it's probably the thing I love the most about life since I left the corporate world in the autumn of 2021, but there's definitely an element of patterns emerging out of nothing. I often find myself doing work on a similar topic with different clients around the same time, or working with clients with similar challenges, or (as in this case) having a number of similar conversations in the same week with people in a similar boat to one another and the serendipity of that is interesting to me.


The conversations were wide ranging, but there was a definite thread which emerged through all of them, about the loneliness of leadership, especially when you're at the very top of an organisation. The nature of a CEO role is that there's nobody above you on the organisational hierarchy for you to talk to/vent to/share with and you have no peers. When you're a leader, it's rarely appropriate for you to vent downwards either; not that it's always the wrong thing to do - there's an element of psychological safety which comes from showing that you don't have it all figured out and you do have things that you struggle with - but it's not something that I'd encourage as a regular approach, given that one of the key roles of a leader is to help create an environment where your people can solve their problems, often with your help. It muddies the waters if you share all of your worries and challenges with your direct reports and can create a situation where they stop sharing their challenges with you, for fear of adding to your already sizeable burden.

A leader cutting a lonely figure towards the top of a pyramid
A leader cutting a lonely figure towards the top of a pyramid

I've seen this particular scenario play out a number of times with business owners who set up their business alone; Firstly, it's just them and the work is all-consuming. They have little time to do anything other than work and they're energised by the challenge and the potential, so they're not aware of being alone. Then they bring in a few close con-conspirators. Suddenly they're part of a gang, probably giving some equity to those early team members and creating a situation of shared success and ownership and vision, so there's no loneliness, because they experience that together, all doing a bit of everything to keep the wheels turning.


But then the business starts to scale and the roles of the team members that the CEO has brought in start to solidify. They go from being a jack of all trades, to a Head of Sales or a Head of Revenue or a Head of Something Else, and they recruit a team to work for them and deliver on their little slice of the strategy. Now, those Heads Of have their own little team, their own little mini-business which they're effectively the CEO of. They've created a microcosm of the business, within the business. As such, they become embedded and engaged within their department and often feel a closeness to that team which, to some extent, replaces their closeness to the leadership team. They have shared goals and targets and expectations with those in their department, whereas they might be at odds with the others in a leadership team (I'm Head of Sales, responsible for selling things, but the Head of Design is responsible for designing things. She wants to design cool, funky stuff but I just want her to design stuff that I can sell and sell quickly because I have targets to meet...)


When this happens, the CEO can start to feel isolated. Firstly, they've (hopefully) built a self-sustaining machine which, to some extent, doesn't need them as much as it did before. The work is divvied up and there are people responsible for delivering those slices, so the CEO is there to set the strategy, drive accountability and perhaps be the public face. And secondly, despite being at the top of the tree and being an owner of the business, they're not a part of any of these teams within it. Each team will have its own targets and enjoy its own successes, which the CEO isn't really a part of. So it's not just about challenge and adversity - sometimes the loneliness is exacerbated in times of success!


There's another dynamic at play in this scenario where the CEO is the owner or at least has some equity in the business but this is not the case for much or all of the team. How much skin you have in the game will typically have an impact on how committed you are to the organisation's success, so your willingness to give up social events and miss special family moments might be very different to that of your people, who see it as a job, rather than a way of life. That disconnect can further the isolation. We saw this week from the backlash to the comments by Brewdog founder James Watt that many, many people work to live and not the other way around and as a CEO who might live to work, it's important to be careful not to project the feelings and expectations you hold for yourself onto your people. Their reality might be very different from yours. You own the company and if the company is a success, it'll probably change your life. They get paid a wage and if the company is a success, that might not change at all.


So what to do, in order to stave off the loneliness and isolation? Well the first thing (and this was important in all of the conversations I had) is to acknowledge it. To surface the unspoken and recognise how you feel. Reflecting on how you feel, rather than pushing it down and hoping it goes away, is the first step to change. Then it might be useful to consider the concept of a personal board room. What support do I need and who can I surround myself with who will give me that. A listening ear, advice, wisdom, good counsel. Who have I had these from in the past? This goes beyond board and general networking to thinking about specific people to fill specific roles. Who has scaled a business in the past who would understand the challenges and have some war stories to share? Who is a great listener, who I feel comfortable being vulnerable and open with? Who is a good, practical problem solver? Would I benefit from a mentor? Would I benefit from a coach? Who inspires me and fires me up when I'm feeling flat? Who has the endless Rolodex of contacts they can share with me? Who doesn't let me off the hook and holds me accountable? What other roles do I need fulfilled around me and who can do it?


Creating this personal board room of 6-12 key people, outside of your business so as to remove any conflicts of interest, who you can lean on and reach out to regularly, can be a fantastic tool to help you celebrate successes, overcome challenges, share doubts and worries and overcome the loneliness of leadership. It all starts with personal reflection and then being intentional about finding and contacting the right people.


I'd love to hear your thoughts and if I can be of any help, please reach out!

 
 
 

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