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Leadership Coaching and Success

What does success look like in the coaching space? Feel like?

There are some obvious, more or less clinical answers. For example, success looks like a client meeting their declared outcomes for the coaching agreement. For some coaches, success might look like a renewed contract. I knew one guy who seemed to measure success by whether or not his clients cried at some point during an engagement. Yes, really. While I think there is a way to define success over the long term, it’s the session by session success that builds powerful outcomes that are often different from the declared purpose of the engagement.

Predictable success

I’ve come to appreciate that in that context success looks like many different things. Part of that is because the goals we coaches set for ourselves are different from person to person and session to session – success is nominally reaching a goal, right?

When I first started coaching, a successful session was one in which I only spoke to ask a question or whether I managed the closing well so that the client was articulating insight and action (success of technique). With some clients, success was getting them to be honest with themselves or to try something (like narrative coaching or one of my frameworks) a little out of their comfort zone. As I got more comfortable with the technical aspects of coaching, a measure of success became, “Good question…” then silence from the client (success of insight). This kind of success leads a client to dig into the process. They become more open and honest with themselves as they grapple with leadership issues (success of trust).

I could probably go on forever, but these and others have become the predictable signs of success for me. Coaches will relate, I’m sure.

Inherently unpredictable

Part of the different look of success is also because the coaching relationship is inherently unpredictable. First, unless the engagement is very structured, we never really know what the client is going to bring to the table on any given day. It’ll be in a particular ballpark (career advancement, managing a team, etc.), of course, but sometimes we start on the mound and sometimes it comes from way out in left field. And the number of times it’s become clear within 15 minutes that what the client said they want to work on and what they come to realize they need to work on is different… well.

Besides, when you build trust, sometimes those topics go deep, into identity, trust, and similar high charge topics. That is always unpredictable. So on some days, success might look like a transformative insight, on others it’s a specific course of action, on others it’s a single moment of radical honesty.

The Feel of success

But no matter what success looks like, it feels very similar every time, for me. I can’t find the right vocabulary to describe it, but it is some warm combination of hope and gratitude. A client a while ago engaged me to coach them on career planning. They weren’t happy in their current role and were feeling crunched at midlife with the way things were going professionally and personally.

Over the six months we had a number of sessions focused on different aspects of the issue, some that looked more successful than others, for sure. But the feeling for me was always this combo of hope and gratitude. I was hopeful for this person that they were grappling and sorting out difficult parts of their relationship to work and building a new outlook on the next twenty years of a career. And I was grateful that they were willing to engage in the process, grateful for the skills I have developed, and grateful for a proven process that I’ve inherited from my mentors and augmented with my own practice. I was also hopeful that their progress would lead them to a happier and more successful life. It was like watching someone searching in vain for a door, who suddenly realizes they’re standing next to an open window and takes a deep breath of fresh air.

So what about success?

Why am I writing about this today? Yesterday, I was working with a team in transition. I’d been working with some of them for about a year, and they developed deep internal trust and a set of very productive processes and behaviors. The team was changing, though, and moving into a different reporting line and part of the organization, so we reengaged for a couple months on that transition. They all (new members and old) knew that they wanted and needed to recalibrate the processes and build new trust. Few of them seemed to feel safe together. While we’d planned for a specific training outcome yesterday, as soon as we were together (unpredictable, remember!) it was clear we needed to pivot. Our session became a group coaching session on internal psychological safety, with an incredibly powerful outcome that day. Gratitude and hope, built on radical honesty and vulnerability. I know that the success was theirs, together. But I also know they couldn’t have done it on their own. Fresh air for everyone.

So, if you’re part of coaching (a coach or a client), think about what success looks like for you, by all means. It’s important and will keep you grounded. But also feel your success and let it feed your commitment to the process, as unpredictable and messy as it is. Because in the end, our goalposts will shift and the external markers of success will change with them. But that feeling when you get there … that will always be the same.

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