Lessons Learned

Common Challenges of Leaders, Managers, and Doers

If you are at an organization, you are one of the following:

  • A leader,
  • A manager, or
  • A doer.

I’ll bet money that no matter how great your job is, you have at least one gripe about your role that “others in the organization will just never understand.”

Well, I’m here to help everyone understand.

Here’s the most comprehensive list of all of the common challenges at each layer of an organization.


They have to anticipate the future based on the macro-economic trends. 

Think about all of the factors they have to consider:

  • Rapidly changing technology
  • Economic volatility
  • Increased competition
  • Changing workforce demographics
  • Supply chain disruption
  • Changing customer demands.

Try to make a quick decision when you’ve got all of that to think about.

They are misaligned. 

A lot of the time, members of an executive team have differing opinions. It’s one thing for leaders to have different opinions, discuss it in a meeting, and come to a consensus. It’s another thing when leaders say one thing in a meeting, but think differently in private. Imagine trying to make decisions when your internal conscience conflicts with your external statements. (Hint: the result is not good).

They don’t have the right behaviors a functional team should have.

Try leading an organization with other executive team-members if:

  • You don’t communicate with each other.
  • You don’t listen to each other.
  • You are unequivocally deferential to the CEO and aren’t encouraged to speak up when you disagree.
  • Nobody want’s to hurt anybody’s feelings.
  • Nobody is decisive.

It’s impossible to lead a company if your leadership team struggles to work with each other.


Are told a strategy without having as much time as the leaders to process it.

Leaders have most likely had meetings upon meetings to come to a strategic decision of what direction to take the company. Managers are stuck figuring out how to make it happen while managing the day-to-day. This can be hard when managers are expected to continue to drive results based on the old strategy, when numbers might drop if they make changes to work-processes that align with a new strategy.

Got promoted because good individual contributors, but lack proper skills to manage.

At Root, we like to call these types of managers the “5-minute-manager.” These managers were so good at doing their job as a “doer” that they were noticed by upper management and got promoted to a manager level. However, managing is not about doing the work you used to do. It is about getting people you manage to do work like you used to do. It’s a whole different ball-game that requires a different skill-set, and more often than not, isn’t one that high-performers know how to play.

Their incentive package does not align with the strategy.

Pretty straight forward here, but when you’re paid to increase the numbers of your department, taking on a strategy and communicating it to your workforce may not be at the top of your list. Ideally, in the long-run it would make sense to follow the strategy, but it’s hard when your paycheck is dependent on short-term performance.

Isn’t told what the strategy means for their team.

In theory, strategies make sense. When you see a line graph going down, doing what we are currently doing, it makes sense to change. But what does this mean for a manager’s team? What literal actions will have to change? This is a lot to put on a manager to figure out, and the better organizations provide managers with the resources to effectively translate strategy into actions their teammates can digest and act upon.

Balance what leaders want with realities of front line

Sometimes, leaders forget what it is like to be on the front line and when coming up with a strategy, they forget to consider the obstacles doers may face when executing a strategy. For example, in the 1990’s when Pepsi decided to expand from soft-drinks to bottled water and tea, they didn’t realize that going from a few SKUs to hundreds of SKUs and going from just aluminum cans to glass bottles would cause heartburn for truck drivers. They needed someone to come help them fix the situation. Can you guess who? (Hint: they ended up working with us.)



Don’t know how their role is connected to the company.

Let’s face it, when you’re out there driving a truck, the last thing on your mind is “what are the macro-economic effects of changing consumer tastes?” Usually, it’s something along the lines of

  • “‘How can I get from point A to point B faster?”
  • “My turn-times aren’t as fast as I want them to be. What can I do to be more efficient?”
  • “What’s for dinner?”

When you don’t engage your doers to think about how your role connects to the purpose of the company, complacency can set in.

Have multiple requests from above, but don’t know what the priority is.

This is particularly the case when the leaders are dysfunctional and give different marching orders every quarter. And, when they do give new marching orders, all of the things that doers were responsible for doing in the past, continue to remain on their plates. New strategies and initiatives should imply that tasks tied to old strategies and initiatives are removed, but that is not always the case.

Don’t have the skill-set required to carry out changes in responsibilities as a result of the strategy.

Sometimes, new strategies require new skill-sets, and the workforce is not trained in those required skill-sets. It becomes incumbent on the company to ensure its workforce is capable of carrying out the strategy.

Has no incentive to change their behavior.

People don’t like change. You better give a good reason to someone if you want to see a change in behavior.

Too focused on putting out daily fires.

It’s one thing to be focused on the new things you must do to help execute a strategy in an organization. It’s another thing to do it while customers are yelling in your ear and there is a mess in the store’s restroom.


For more information on this topic, click here.

Steven Choi works at Root, Inc., a Strategy Execution Company. He helps align organizations – all the way from the leaders at the top, to the truck drivers out there in the field.

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