Get Out of the Weeds: How to Balance the Day-to-Day with Overarching Strategy

One of the most frequent struggles I see with entrepreneurs and business owners is this tension between managing the day-to-day operations of the organization and focusing on overarching strategy. 

In the earliest days of a company, most entrepreneurs have to do both. And most of them hang onto that role for far too long, spending too much time in the weeds when they should be looking at the bigger picture. 

Many business owners who seek coaching or peer advisory boards know they’re not spending enough time on strategy, and they can’t figure out how to shift the balance. 

Are you in the weeds?

If you’re questioning whether you’re in the weeds, you probably are. When you’re spending a significant amount of time working on high-level strategy, you know it. 

Stephen Covey’s time management quadrants are a helpful way to get honest with yourself about where your time and energy goes. 

I spoke with a client recently who couldn’t decide whether to hire an assistant. They weren’t sure whether they really needed it, or whether they could afford it. When we evaluated this client’s time, we saw they were spending lots of time in Quadrants I and III — on crisis issues and in meetings, phone calls, emails. 

They were spending almost no time in Quadrant II — on the strategic issues that are not urgent but are critically important to any organization. They weren’t doing the long-term planning, the relationship building, the opportunity assessment. 

This client was hustling. And when you’re hustling, you’re almost never being strategic. 

If you’re in constant crisis mode, if you have your hand in every pot in the organization, if you spend 99% of your time crossing items off a to-do list or in meetings, if you’re making detailed corrections to employees’ work: you’re in the weeds.

The way to get out of that hustle mode is to delegate. 

How to get out of the weeds

Chances are, if you’ve started a business or are a leader in an organization, there’s a bit of a control freak in you. There’s no shame in it — lots of entrepreneurs and business owners want to be in control. The most important thing is to know that about yourself so you can mitigate that tendency when necessary. 

There’s nothing inherently wrong with wanting to control things. The problem comes when that desire stands in the way of your progress by keeping both you and your team members from doing your best work. 

Making a change won’t be comfortable, though it will be worth it. 

See: How to Delegate Like a Boss

Step one: identify the tasks only you can do

When you don’t focus on strategy, your organization becomes less resilient, less able to respond to change. You lose opportunities for growth. 

So what are those strategic activities that only you can do? Are you the only person who can decide the next area of focus for product launches? Are you the only person who can meet with potential investors? Are you the only person who can build brand partnerships?

The tasks on that list are what you should be spending the majority of your time doing. That’s how you can provide the best value to your organization. 

You’re probably doing lots of things that aren’t on that list. That’s where step two comes in.

Step two: assign jobs to the right people

Stepping out of the weeds is difficult. You’re going to question whether you can really trust someone else to deliver on whatever it is you’ve been struggling to delegate. 

That’s why it’s critical that you’re delegating to the right people — people who subscribe to your organization’s core values and who have or can develop the skills necessary to be responsible for the relevant tasks. 

You’re going to have a much harder time delegating employment issues to your head of HR if that person is an office manager you promoted because they’re “good with people.” The person you’re assigning responsibilities to needs to have the skills to carry them out or be in the process of training to attain those skills.

See: All Employees Should Have a Professional Development Plan. Do Yours?

Create check-in and feedback structures

Delegation often goes awry when leaders use a throw the baby out with the bathwater approach. They recognize they’ve been too involved and need to hand over responsibility to someone else. So they assign a huge project to an employee and tell them to come back in a month with the finished product. 

The employee is inspired by the confidence their leader has shown in them and is determined to do a great job. Except that around two weeks in, they start to question whether they’ll meet the deadline. They struggle to decide between two different directions. They get bogged down in research. 

By the day of the deadline, they’re weeks behind and have few results to show for their effort. On the other side of the desk, the leader has been holding their breath, waiting to see if this delegation thing could really work. And here is their proof that it doesn’t. 

Of course, the project would’ve been totally different if they’d scheduled weekly check-ins — not for the leader to step in but for them to answer questions and provide necessary coaching. 

Weather setbacks by focusing on the big picture

When a delegated project doesn’t go well (and that will happen at least once), you may be tempted to take back responsibilities. 

Instead, remember the bigger picture (you having space to work on overall strategy) and take the time to evaluate the process for that project. 

Did the team member have all the information they needed? Were they lacking a skill that could be addressed with additional training? Was there a misunderstanding that could have been avoided by more frequent check-ins? Would a different person have been the right one to handle that delegated responsibility? 

Provide helpful and honest feedback to the employee so their next project is more successful. 

See: The Coaching Process: Coaching Your Team

Final thoughts

Having a dominant personality, being directive, liking control — these aren’t bad traits. In fact, for many entrepreneurs, they’re incredibly helpful. To a point. 

The key is to know when to be in control from a distance, determining the overall direction and not the day-to-day minutiae. For some, relinquishing that control is relatively easy. They automate as quickly as they can. They’re excited to pass along tasks and move into their CEO role. 

They say, I didn't build this company to do all the work. I didn't build this company to wear every hat. I didn't build this company so I could work 80 hours a week. I built it so I could live the life I’ve always wanted.

And then there are the entrepreneurs who are saying that same thing to themselves — but with frustration — because they can’t seem to get out of the weeds. 

They may need support to move out of their comfort zone so their organization can be successful. We help in-the-weeds entrepreneurs and business owners all the time (it’s a common problem).