Coaching: a Habit, Not an Event

Over the years, I have read hundreds of books (seriously) on organizing, productivity, and dealing with paper (I HATE paper). Along the way, I have also hired several professional organizers to help me set up supportive and quite beautiful systems.

And yet, until recently, if you’d visited my home office unannounced, you’d have seen piles on every flat surface — stacks of books, mail, and training materials. It felt like they were multiplying daily and I couldn’t find a way to get in front of them.

Until this past summer. That’s when I put a new approach in place — one that has nothing to do with Marie Kondo techniques or streamlined organizing tools. Instead, I adopted a simple habit: take small “bites” on a regular basis.

So, every Monday morning, I deal with everything in my inbox (both hard copy and virtual). I go through it, act on it or add it to the to-do list for later, scan it into a digital folder, or throw it out and move on.

Now, not only are things in much better shape (not perfect, but I wouldn’t cringe if you stopped by unannounced!), but I no longer feel dread from having a huge organizing project always hanging over my head.

As I’ll explain in a minute, the best coaching works the same way.

Time is the Limiting Factor

Recently, we surveyed leaders on LinkedIn by asking a simple, multiple-choice question: “When it comes to coaching employees, what’s your biggest challenge?”

The options included things like “knowing what to say,” “navigating emotions,” and “turning conversations into action.” But the top response (by a wide margin) was, “finding the time to coach.”

That’s right. The primary reason leaders don’t coach more is not that they don’t care, or don’t know how, or doubt coaching’s value. Rather, it’s because they are stretched so thin they just can’t figure out how to squeeze coaching into their already packed days.

Coaching as Daily Practice

Somewhere along the way, we got the idea that coaching needs to be formal, documented, and at least an hour long. Who wants to deal with that? So leaders put it off until later… you know, until after their “real” work is done.

A better approach is to offer quick, meaningful moments of focused attention — to shift someone’s perspective, troubleshoot a challenge, or boost their confidence.

Besides, coaching isn’t just a nice-to-have. It’s actually the lack of coaching that creates most of the interruptions, rework, and time drains that keep pulling you back into the weeds. Coaching doesn’t steal your time; it restores it. When people get the support they need, they grow more capable and confident — and less dependent on you.

Some suggestions for putting this into practice…

Include Coaching Moments in Your Existing Touchpoints

You don’t need to schedule more meetings; you need to use the interactions you already have differently. So look for natural openings: when someone asks for help, at the end of a regular one-on-one, during a project update, right after a customer call.

These tiny moments add up and require no extra time on your calendar (isn’t that a relief?). Consistency, not time spent, is what will help you make the shift. Eventually, as coaching becomes part of your day-to-day leadership, it will feel less like an overhaul of your personality and more second nature.

Swap Advice for Questions

When someone presents you with a challenge, instead of instantly giving your answer, ask one or two coaching questions to help them think it through: What have you tried so far? What other options do you see? Who else needs to be involved?

Questions develop capability in ways advice can’t. Over time, you’ll notice people coming to you not just with problems, but with really good solutions (often even better than the ones you would have suggested).

Create Brief, Consistent “Drop-Ins”

Just like I schedule Monday mornings for organization, you can set aside a few 15-30 minute blocks each week where your team knows they can bring decisions or challenges.

By providing them with predictable access, you will reduce the constant interruptions and establish a rhythm that makes coaching feel easy and sustainable. (Dare I say, even fun?)

Always Be Coaching

After nearly twenty years of coaching leaders, I can say this with complete confidence: Coaching isn’t something you add on to your leadership — it is leadership.

But if you turn it into a big, formal, overwhelming project, there’s a pretty good chance you’ll keep pushing it off. A better approach, like keeping an organized office, is to take small, meaningful, regular “bites.”

Try that and watch as your people grow and thrive.