Box of Crayons Blog


How to Coach Like a Leader … Even (Especially) When You’re a Skeptic

You know who you are. You’ve been hearing about coaching (or mentoring, its first cousin once removed) for years now and thought, “Yeah, yeah … that’s for those HR / ‘people people’ types, not me. I’ve got a real job to do.”

Or perhaps you’ve figured out how to do pseudo-coaching. You don’t tell people what to do directly, just cunningly ask, “Have you thought of …?” (Which is not so much a question as it is advice with a question mark at the end.)

Or perhaps you’re just too busy. You’re certain coaching and mentoring takes too much time, and as much as you’d like to sit down for a nice chat with everyone, you’re already overcommitted and overwhelmed. There’s no room for anything extra.

There’s Good Reason to Be Skeptical …

As our world has become more complex and more millennial-y, coaching’s importance to successful teams and organizations has only grown. If you work in an organization of any size greater than one, you’ve probably been encouraged to coach those you manage and lead. But what’s good in theory is proving difficult to put into practice.

A 2006 report from leadership development firm BlessingWhite suggests that 73 percent of managers have had some form of coaching training. However, it seems it wasn’t very good coaching training. Only 23 percent of people being coached thought the coaching had a significant impact on their performance or job satisfaction. Ten percent even suggested that the coaching they were getting was having a negative effect. (Those must have been miserable meetings.)

No wonder there are skeptics. And skepticism is okay.

… Just Don’t Be Cynical

The word cynic comes from the Greek word kynikos, meaning dog-like. In other words, they’re going to cock a leg on it, no matter what. Cynics have written the whole thing off, regardless of the evidence.

Skeptics, on the other hand, are pretty sure it’s not worth it … but are willing to be convinced otherwise. So skeptics, let me tell you why you should consider being more coach-like.

  1. You help those you lead

Dan Pink laid it out beautifully in his book Drive, which shows that what really motivates people is not so much money and status but autonomy, mastery and purpose. There’s no faster and cleaner intervention than asking a good question — the essence of being more coach-like — to drive autonomy (they answer it, not you), mastery (questions create aha! moments; advice does not) and, to a lesser extent, purpose (if the question helps make the connection to the why of it).

If you want those you lead to be more engaged and to increase their capacity and potential, asking a good question will do it.

  1. You help yourself

One of the Box of Crayons’ coaching principles is Be Lazy. Which always makes people in the audience twitch when they hear it. Because, like you, they’re hardworking, ambitious and driven. Being lazy is anathema to their DNA. But here’s what happens when your ambition leads you to be the advice giver, solution provider and answer finder for those around you. First, you create an overly dependent team, a team that comes to you at first for a few things and then eventually for everything, because you’ve trained them to do just that. This is not a motivated and engaged team; this is a codependent team.

Second, since you’re now doing the team’s work as well as your own, you feel the cold waters of overwhelm lapping at your feet. You’re overcommitted and stretched thin. And because you’re now focused on just trying to get it all done, trying to do what Cal Newport calls deep work is impossible. You lose that sense of connection to the meaningful work, Pink’s “purpose” work, your Great Work.

Asking a good question is a self-management tool to stop you from leaping into action. If you’re asking, you’re not doing. In short, getting good at regularly asking powerful questions will let you work less hard and have more impact.

A New Hope: Three Counterintuitive Principles

Now, let’s be clear here: we’re not trying to turn you into A Coach. There are enough of those already in the life-coaching and executive-coaching fields. We do want you to be more curious and coach-like as you lead. That’s something that can be done by everyone, and in a way that will have a significant impact on performance and satisfaction.

But to make it work for the busy and skeptical manager like you, you’ll need to follow three principles that break the current rules:

  1. Keep coaching to 10 minutes or less. If you can’t, you don’t have time for coaching.
  1. Keep it simple. You don’t need a psych degree or to understand fancy coaching models. Seven good questions and the discipline to make asking them a habit is all you need.
  1. Strive for drip irrigation (not the occasional flash flood). Make coaching a regular act by transforming the interactions you have, rather than adding more to your workload.

Here is how to put these principles into action.

1. Notice your default response

A recent survey by Harvard Business Review asked people to self-identify what style of leader they are from eight possible choices. The top pick at 23 percent was Collaborator — described as “empathetic, team-building, talent-spotting, coaching-oriented.”

We think they’re delusional.

Most managers are terrible at being coaching-oriented, at being curious. Just as doctors (a study found) wait only about 18 seconds before interrupting their patients, most managers move into advice-giving, solution-prompting, and answer-offering mode almost instantly.

When you’re in a conversation, notice how quickly you trade curiosity for giving advice. You’ll be shocked at how quickly it happens.

2. Pick a question

The Coaching Habit offers up seven essential questions all managers and leaders should have in their repertoire. We suggest you start by picking one — the one that feels most useful to you — and giving it a shot.

It could be the Kickstart Question: “What’s on your mind?” It’s an effective way to start a conversation and get more quickly to the heart of what matters.

It might be the Focus Question: “What’s the real challenge here for you?” It’s easy to be seduced into thinking that the first challenge is the real challenge. It rarely is.

Or it could be the Best Coaching Question in the World: “And what else?” Because you’ll find that the first answer someone gives you is never the only answer, and rarely their best answer.

3. Build a habit based on your question

Charles Duhigg’s The Power of Habit was a catalyst that got people focused on the science behind habits, the building blocks of a better life. Borrowing some of his insights, along with the “tiny habits” of B.J. Fogg and insights from others, we’ve developed a simple model: The New Habit Formula. Its three parts are:

“When this happens …”

Identify the trigger — the situation in which you’re looking for a different response. For example: “In my weekly meeting with Monica, when she asks, ‘What should I do? …’”

“Instead of …”

Identify the old behaviour — the habit you’re looking to change. To continue the example: “Instead of my telling Monica the answer …”

“I will (in 60 seconds or less) …

Define a new habit. Fogg says to define any new habit so it takes less than a minute to do. To finish our example: “I will ask Monica, ‘What’s the real challenge here for you?’”

Stay Curious, My Friend

When we feel the pressure to get things done, it’s all too easy to default to giving advice and providing solutions, achieving only a Pyrrhic victory. Adapting the principles and practices of building a coaching habit may be a little uncomfortable at first — for you and for the people you lead — but the upshot is you’ll work less hard and have more impact. And even the skeptics are interested in that.

6 Responses to How to Coach Like a Leader … Even (Especially) When You’re a Skeptic

  • Hatty

    Succinct but packed with ideas that you can ‘give a go’ from ‘now’
    Thank you.

  • JB

    Love the idea of “drip irrigation” – building a coaching habit into my current interactions rather than adding to my workload.

  • David Cartwright

    Excellent post; just launching our new discipline Coaching in Leadership and will use this as one of our learner references…please.

  • Anne Morgan

    Brilliant advice, especially for those who feel huge pressure to supply all the answers. Putting a break on that urge and patiently coaxing people to reveal the real problem is a great skill to acquire.

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