What Business Problem Is Keeping You Up At Night? - GROW GREAT Podcast Episode 4003

4003 What Business Problem Is Keeping You Up At Night?

What Business Problem Is Keeping You Up At Night? - GROW GREAT Podcast Episode 4003

In the morning the bed looks like we’ve been wrestling a bear. We tossed and turned until we finally got up. We read a bit. Browsed the web some. Even tried to watch something on Netflix, hoping sleep would eventually come. It didn’t. Not much of it anyway.

In spite of connections, sometimes found all the world — and in spite of service professionals like attorneys and accountants — and in spite of a terrific inner circle of direct report managers who are extremely capable — CEO’s can be among the loneliest and most sleep deprived people on the planet. I once considered hiring myself out at night for sleep study research figuring I might as well get paid for not sleeping. A capitalist to the core!

Recently, I was discussing all the compliance requirements required of financial advisors. With a financial advisor. The money, time and HR investment required to wrestle that problem was staggering to me. Forget your politics. Or mine. Well, I don’t have any really – except not being fond of anything that hampers our ability to operate in a free-market when we are committed to doing the right thing. But my business mantra has never been very sophisticated or hard to understand…


Small business owners will readily mount a pulpit anytime talk turns toward compliance issues, regulatory restrictions and tax rates. As I’m listening to this business owner talk of how daunting it is to maintain compliance with all the regulations, she says, “I’m afraid to do a break-even analysis on my compliance costs, but I should do it.” We agreed it’d like being sick, but not knowing what’s wrong. Ignorance is not bliss. It can be deadly. Her firm was handling the expense – they had no choice – but she was concerned with the ever mounting cost in both time and money. Couple that with the pressure to deliver more dazzling service to customers at lower and lower costs. It was an old, old refrain I’d heard many times since I first stepped into a hi-fi store at 16 to begin my first sales job.

Business problems.

That keep us up at night.

I’m happy to say that more often than not I’ve found business owners and CEO’s who were proactive, but that’s no surprise. Typically these are people with strong determination, tenacity and resiliency. If they weren’t, they wouldn’t likely be where they are. That doesn’t mean they’re successful in operating their business though. Or that they’re good at managing the issues confronting them and their business. Some are. Some aren’t. Some do well most of the time, but a sudden unforeseen challenge can lay them low.

In just the last few months I’ve heard of 3 CEO’s who are going through a divorce. The holidays seem to be a favorite time for some people to decide, “Enough.” As I listened to one story of a divorcing CEO I could hear the pain and sadness in his voice. It was apparent in his face. And I thought, “There’s no way this is staying out of the office.” How could it? Impossible.

I’m sure he’d had many, many sleepless nights leading up to this final death knell on his marriage. I’m equally sure most people at work had no idea. But those closest to him had to know something was wrong.

Conversation turned toward those circumstances and how employees left to wonder, “What’s wrong with the boss?” can lead to some really awful cultural collateral damage. As bad as his divorce was for him and his family, the employees were likely thinking of something far worse — something that impact THEM. It’s reasonable. It’s not that they’re uncaring about their CEO, but they have their own families. Their own concerns. Their own dreams. He’s the boss though. And his life has a direct impact on theirs.

True servant-based leaders shoulder that burden, too. They understand how they impact the lives of their employees. And vendors. And financial partners. And customers. Just keep piling on that weight until our knees buckle, right? As the sign in my office says (bought by my daughter who no doubt has grown tired of hearing me say it repeatedly)…


Divorce? A business problem? Yep, it sure is when you own the joint or you’re the CEO. A flat tire on the way to work that vexes you, is also a business problem. Especially when you hit the door ready to bite a nail in two.

Then there are those strategic and organizational issues. Compliance stuff. Industry disruptors. Technology challenges. The every present people problem of finding the right people and putting them in the best spots, then hanging onto them. There are inventory problems, payroll problems, lease problems, sales problems, cost containment problems, distribution problems, pricing problems…the list just keeps on going. Pick your poison.

I know the pain very, very well. Through the years I’ve also learned a thing or three about handling them in a way that moves me from being uncomfortable to being positively action-oriented toward a workable solution. Heavy emphasis on workable. Some solutions are pie in the sky or completely unreasonable due to expense or the take required. While none of us enjoy fire-fighting, sometimes there is a fire. In those cases, it’s grab the management equivalent of a fire extinguisher and get the blaze under control. Worry about the damage later. First, stop the fire from burning the joint to the ground.

4 very practical and effective steps to conquering the demons that keep us up at night

a. Plan your attack, even if the plan is imperfect (and you know it)

You’ve heard the adage that even a bad plan beats no plan. Well, it’s certainly true when it comes to the issues that keep us up as CEO’s or business owners. The toughest thing is the wondering what we should do? Our minds get on that hamster wheel of wondering and questioning. Should I do this? Should I do this?

The longer you stay in this land of limbo the more sleep you’re going to lose. And the more weary you’ll become. This is the sleepless death spiral that we’ve all experienced when we’re just vexed and frustrated (and worried) beyond the everyday issues we regularly face. Come on, most problems don’t keep us up at night – thankfully. But these – these elephants in the room – prevent those sheep from entering our room as we can count them and get some shut eye.

What’s the very next step you need to make? Who do you need to call? What do you need to do? Right now.

This can be much, much tougher than it sounds because as CEO’s and business owners we want to connect the dots all the way to the end. Sometimes, we’ll spend too much time trying to do that, only to find that we missed a dot, or we connected two dots that never should have been connected.

Besides, there are circumstances that our next one step will likely bring about that we may have never seen coming. The issue very well may change once we head in the right direction.

So, while you’re up tonight pondering the problem, wrap your head around answering this question…

What one thing can do right now or first thing in the morning to start fixing this problem?

It’s a one-step plan, but it’ll fuel your mind to think more clearly about the step after. Right now, you just need to do something meaningful knowing that you can always retreat, pivot and morph your ideas to suit the situation as it more fully develops.

This step prevents crisis management when crisis management isn’t necessary.

b. Don’t overthink it and delay.

Most of us are prone to overthinking after the fact. By nature, most of the CEO’s I’ve ever known were decisive people able to make fast decisions with very limited (but compelling) information. That’s not hard for most of us. What may be hard is doing that in our mind – making a decision – then prior to execution we begin to wonder if we ought to do something else. Or maybe we wonder if we should just delay an hour, or a day. Or two.

Delay causes greater vexation. Vexation in a CEO causes untold anxiety throughout a company. The ripple effect I talked about last time in a CEO’s own professional development (see episode 4002) works in reverse here. When the CEO is fretful it ripples to everybody around him and pretty soon the whole place is worried. That’s too high a price to pay for putting off what you can do right now – even if what you attempt right now isn’t the perfect or final solution. At least you’re trying.

And you’re trying right now. Besides, you want to show your people how important speed is in handling problems. You want to lead a remarkable, decisive, proactive organization. Then you’ve got to be remarkable, decisive and proactive under the most intense pressure.

c. Make your next move based on new information.

I don’t play chess, but my son used to play quite a lot. Every now and again I’d play him. I understood only enough to know how the players can move. He understood the strategy, something I never learned.

He’d begin by making a move. I’d make a move. My move would impact the move he made, especially later on in the game.

That’s how this problem should be handled. You make a move. Maybe it’s ideal. Maybe it’s not. No matter, it’s not going to be wrong for long because based on the outcome you’re going to make adjustments. Depending on how your first action impacts the situation you’ll decide what to do next.

Did your first move seem to lower the pressure of the problem? Great, then now what are you going to do? Take in that new information and make adjustments.

If your first move made matters worse, then you have to take action quickly to reverse matters. Either way, your next step is based on the impact your first step had on the situation.

It’s what you do in running your business. You’re always looking for data to support whether we’re moving up or going backward. And the faster you know the faster you can adjust. Sometimes the trend is slight. Other times it’s extreme. But as the CEO we’re hungry for data. We need feedback to know how good our aim is. So go ahead and take that first shot, then look closely at the target so you’ll know how to better aim the second shot.

d. Keep doing it. Rinse and repeat.

The more we take action the easier it is to keep taking action. The more we worry about something, the easier it is to keep worrying. You decide.

Action or worry.

Action may keep you up at night, but only because you’re working. Worry on the other hand will keep you up at night and exhaust you.

Weary leaders shouldn’t remain weary for long. The company is looking to you for leadership. A sleep deprived CEO in a funk isn’t fit for the battle. So get battle ready and stay that way…because your business depends on it.

FREE! 90-Minute CEO ONE-BIG Thing Introductory Coaching Session

If you’re awake at night because there’s one big thing that is frustrating you beyond words, then I’d like to offer you a solution at no cost or obligation. Just click here to find out more.

Thanks for listening. Get some sleep.


Subscribe to the GROW GREAT podcast

bula network podcast on itunesTo subscribe, please use the links below:

If you have a chance, please leave me an honest rating and review on iTunes by clicking Review on iTunes. It’ll help the show rank better in iTunes.

Thank you!

Scroll to Top