What Keeps You Awake at Night?

Apr 23, 2024 | Growth Tips, Leadership, Management

What keeps the owner awake at night?

If you are a manager, this is an important to question to ask your boss. It’s key to “managing up.”

If you are the boss, its important to let your team know what’s going on in your head.

It’s a metaphor:

Even if you sleep well, you still have challenges that you would like solved.

We get to the bottom of this question during our consulting projects; solving the big challenges on the owners mind.

We also use this question when helping seconds in command to work better with their owners. A good #2 needs to be able to read their boss’s mind.

So what keeps you awake?

The answers to this question fall into five categories. Some are amusing, but they are all real.

Five Top Challenges That Keep Owners Awake At Night.

1. My Newborn.

Family comes first, especially when it’s a new family. Though I have personally found that older children can take up just as much time. 😉

Moral: Make sure your team or second in command can rise to the occasion, and run the business so you can take care of your personal business.

Don’t wing it, plan for it.

2. Politics.

There is nothing you can do about the Presidential election. Sometimes the economy has a hiccup during an election year, but not always.

History shows that the economy and stock market does well (or not well) under both parties.

Our economy is driven by entrepreneurs and our capitalist spirit, the President controls less of it than you would think.

Moral: Don’t fret about things you can’t control. Pay close attention to your local market and your own company and ambitions.

3. Employees and Culture.

Every leader wants to protect their culture, and sometimes they need to deal with difficult employees.

These two are connected.

Too many companies hold on too long to the wrong employees.

  • The owner thinks the employee is critical to operations.
  • Suddenly the pain becomes too great, and the employee gets promoted “to another company.”

In hindsight, the owner will say “our team rallied, and we didn’t skip a beat; we could have done this much earlier.”

Moral: The best route to protecting your culture is actively fixing the broken links.

4. Keeping Momentum.

Many of our clients had a great 2023, and the question that keeps them awake is, “How do we maintain the same level of hunger in our team in 2024?”

There is not a single or simple answer to this question.

(But) it’s key to have a refreshed purpose or new set of goals to keep the team focused.

It can’t be the ‘same old, same old’.

Also, your team will go through walls for you, but don’t let them break their nose while doing so.

Moral: Take care of your team while keeping them inspired by the current challenges and future goals.

5. Handling Growth.

The final item that keeps owners awake is preparing the organization to handle the growth.

Do you have the right team in place to get you to the next level, and to handle it once you arrive?

Because “what got you here won’t get you there.”

It helps to periodically think ahead 3-5 years, and consider the systems, positions and capabilities you need.

As in car racing, you have to plan 3-4 turns ahead (i.e. 3 steps ahead)

Moral: Your success tomorrow is based on moves you made yesterday.

Your Challenge: Find out what keeps your team awake at night as well.

It’s not just the owner who thinks about work when they go home.

Any team member with an ownership mentalitywill carry that burden with them.

Find out what keeps your team awake at night, and help them solve the controllable issues and relieve the undo pressure.

Regards, Jeffrey Scott!

P.S. Did you forget to sign up for our Summit? We still have the “early bird” discount in play. But the hotel rooms are selling out fast, so act now.