The hardest leadership advice to follow

We all know we’re supposed to “work on the business and not in the business” as a leader… but what holds us back? And, how do you exactly put “stepping away” into practice?

“Work on the business, not in the business. Pause. Step back. Take stock. Reflect. “

This is some of the most ubiquitous advice I’ve received from leaders on our podcast, The Heartbeat, over the past few years. Yet, as often as it’s repeated, I wonder how often it’s followed.

I’m writing about myself here, namely. Yes, conventional wisdom says to “sleep on it”, to step away from the work to get a fresh perspective on it. And yes, I’ve vigorously nodded my head in agreement whenever someone espouses something along those lines. But, if I’m being honest with myself, how often do I personally act on that recommendation?

For the longest time, my answer has disappointingly been, “Not often”. Prior to last year, I didn’t regularly set aside blocks of meaningful time for myself to reflect on the business. When faced with a critical decision to make or a tough situation to resolve, I plunged myself deeper into the work.

“More, harder, faster” was my default setting. Is it yours, too?

Sinking in

Sometimes, a thing has to smack me aside the head for it to sink in. Case in point: It wasn’t until I’d accumulated the mass repetition of the advice, “Step back, reflect on the business,” over and over again, that I woke up to the obvious wisdom that’d be staring me in the face all these years.

My ears perked up, in particular, this past fall when I interviewed Natalie Nagele, CEO of Wildbit. I asked her about the biggest lesson she’d learned running her multi-million dollar company for the past 17 years, and she said this:

“In order to truly lead, we have to have time to think and to really step back and work, as cliché as it is, on the business and not in the business. You know that it’s important. You read about how important that is. Everybody tells you how important it is. All your mentors do it, but you’re still a small business and you’re stuck in so much of the day to day.”

Natalie’s words resonated with me. She admitted firsthand how it’s a well-known platitude to “work on the business and not in the business.” And yet, she also admitted how hard it is to do in practice. (What a relief, I wasn’t alone!)

But why? What keeps us from doing this thing, that so many of us know is good for us as leaders to do?

The big hairy monster of “now”

The biggest culprit in the room is the urgency of the situation we’re in. Some giant, hairy monster is in front of us now, waving his hands madly, saying, “We can’t afford to slow down, and stop doing something. Someone just put in their two weeks notice. A client is (rightfully) freaking out about a poorly delivered project. Another client is giving you a hard time (unjustifiably) about something you have no interest in doing. Two team members are having a personal dispute and you’re going to need to step in. Oh, and that new potential hire you were so excited about? She just accepted another job so you have to go back to the drawing board for that role…”

For many of us, the hairy monster doesn’t stop yelling, he doesn’t stop waving his hands. Especially, in a small team, it’s all we can keep our eyes on.

How many hairy monsters do you have bopping around?

Making the monster less scary

Natalie had an insightful response to our tendency to be focused on the unexpected problems, the sudden fires, the hairy monsters constantly in our view. She told me that those hairy monsters of big decisions and tough situations are “a lot scarier when you’re in the business than when you take a step out.”

For instance, let’s examine the hairy monster of a key person about to leave. Whether it’s a walk over lunch or a day you take off to mull on the situation – the reflection will likely lead more lucid thinking. You’ll have time to ask yourself questions like: “What’s the worst case scenario? Can we replace this person? Does this person leaving open an opportunity for us to improve our culture in some way?”

Distance and time from a problem often removes the fear, insecurity, or anxiety associated with it. As a result, you can act with clarity and decisiveness. You’re not posturing nor pretending things are great – rather, you’re choosing to see things for what they are. You can respond, instead of react. You can see that the big, hairy monster isn’t so big and hairy as you initially perceived.

Looking back, the best decisions I’ve made have been in this way: With thoughtful deliberation, careful time set aside, and a true stepping away from the business, be it for 10 minutes, 10 hours or 10 days. And the worst decisions I’ve made? They conveniently have all been made when I was rushed, flustered, or fearful.

Similarly, Natalie shares how her worst decisions were made when she didn’t take the time to step away. She leveled with me: “I’ll come back to [a decision I made under stress] three months later but that was a really bad decision, like, ‘We should have not have reacted that way.’”

In my interview with Joel Gasgoigne, CEO of Buffer, he attested to this as well, sharing a metaphor that likens the mind to a glass of water. When he is first faced with a difficult decisions, Joel describes:

“I’ll now just say ‘I’m not in the right state of mind to make this call right now, I’m going to go away and think about it, just overnight.’ It might not take long. It might have taken an hour from being away from that. Then this cloudy glass of water settles, and then I have this clear mind on it. Usually for me, that’s when I have the epiphany of, ‘This is the right thing.’”

So, how do we clear our mind, and make our glass of water less cloudy?

Letting the water settle

Natalie shared how she regularly schedules 3-day retreats with her husband and business partner Chris to go up into the woods, and focus on a particular issue. Nick Francis, CEO of Help Scout, took a month-long sabbatical, coming back truly refreshed and clear-eyed from the vacation (you can read more about his experience here). When Bill Gates was still CEO of Microsoft he would take a week off every year to sit in the woods and think without any distractions. And, John Donahoe, former CEO of eBay, has talked about how he takes a “thinking day” approximately every three months.

For myself this past year, I’ve scheduled one half-day – either on Monday or Friday – every week for long-term thinking about the business. And then, every month, my business partner Daniel and I will take a full day to do a strategy session. It’s our way to clear the muddy water, to chase out the hairy monsters, to work on the business and not in the business.

If you don’t already take time to step back and reflect on the business, perhaps now is the time. Don’t, like me, wait until tens of other successful leaders have told you how helpful it is for them.

This truism is true for a reason.


Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

5 thoughts on “The hardest leadership advice to follow

  1. This is so important, even for “one-person” freelance businesses like mine! I recently started holding a Meeting With Myself on Fridays, and so far I feel like my sense of what I need to focus on for the future and how to grow for success is lightyears ahead of when I was just consumed with the next task, the next client communiqué, the next invoice, etc.

    Thanks for the great writeup.

  2. Love this, Claire! I needed it. It’s so incredibly tempting to dive into the doing and forget about the thinking. I also think, at least in my case, not doing the thinking is somehow rooted in a fear of actually not knowing how to solve the bigger challenges that I know I will have to handle if I start the thinking. It’s easier just to dive into work that I know how to do and tackle problems I know how to solve. But growth and development (both your own personal and that of your organization/business) will never happen if you don’t step back to reflect on where you’re going.

  3. Your primary role is: growth. That includes a long-term vision and time. If strategy is your main concern you stay big picture and rely on others to implement the plan. The reflection part makes sense because you’re evaluating what worked and what didn’t. It’s hard to do because most business owners like to get their hands dirty. It’s similar to the transition of a new manager. Different role. Different skill set. Give yourself some grace in terms of time needed to adjust. But do step back and evaluate your role too.

  4. Thanks for the reminder, Claire. I think the busier we get, the more space we need in our lives to step back and reflect. One way I create that space for myself is to set aside 90 minutes to an hour every weekend to review the past week and plan for the following week. It’s easy to try to do it all, but for me, it’s about doing fewer things better, now as well as later.

  5. Great reminder and I wonder if thinking about it differently (in the way you written here) will help us all take that time.

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