Stuck and Struggling: the Can’t-Let-Go Leader


I’ve helped lead sales/marketing for 2 small and growing companies (10 years each); plus, done all the business development for my own consultancy for the past 8 and a half years.

And, I’ve consulted with dozens of companies and startups on their strategy and messaging.

In other words, I’ve seen a lot of what happens when small-ish companies try to get to the next level. It’s not always pretty.

What goes into companies getting stuck, and struggling to grow and find their “fit” in the marketplace?

Let’s explore. I’m not sure how many posts this series will take. And I definitely want your input as well, since we can all learn lessons from a variety of perspectives (you’ve seen “stuck” companies in situations I’ve never encountered).

I’ll start with this huge issue: the Can’t-Let-Go Leader.

Stuck Leader 1

Usually, this is the founder of a company. It’s his or her “baby.” And in getting the company off the ground, this leader had to do it all (literally) – product development, sales, marketing, partnerships, account management, finances….it all rested on one set of shoulders.

The buck started here, and stopped here. In the founder’s head, and bank account.

Soon, more people had to be hired, for specific tasks, but the leader had the luxury – for a season – of still having a hand in everything. It was a matter of quality, it was a matter of control, it was a business form of helicopter parenting.

It is, after all, my baby.

You’ve seen where things go next, right? As the company grows, more people are needed. Talented people, with leadership potential. Responsibilities begin to spread out. And then the company, and its leader, arrives at the crucial crossroads.

How do I begin to let go? Do I begin to let go?

One of the factors at play here, if we might dip a bit into the psychology of it, is an identity shift for the leader. As much as he/she may have moaned and groaned over wearing so many hats, may have complained about finding responsible employees, there’s a certain self-importance that operates below the surface. It’s not unlike the identity struggle that parents have when their kids begin to become self-sufficient.

And some leaders can’t make the transition. They can’t let go.

Here’s the truth – any company founder or leader is going to be best at one or two things, and weaker at others. Some are great creatives and marketers. Some are visionaries, while others are operational geniuses. Some excel at people management, others can sell light bulbs to Old Sol himself. Starting a company and running it in early stages can be accomplished with these imbalanced skill sets; but ultimately, reality and humility and trust have to settle in.

You need others who are complementary in their strengths, and who can drive whole new levels of growth. Every Steve Jobs needs a Tim Cook.

One of the symptoms of the Can’t-Let-Go disorder? All of the strong and ambitious people eventually leave – and sometimes they leave ugly, because of the choking frustration. I’ve seen this happen multiple times – in companies, in families, in churches.

So, if your company has hit a ceiling in its growth, and seems to lose key people, maybe the answer is in the mirror. Learning to let go, and to put new structures and people in place, may (will) take some months of painful transition. But the alternative is to be stuck on a treadmill, anxiously carrying the weight of an entire company on your back.

You’ve got to learn to let go, in order to grow.

Maybe you’ve been “that leader” – if so, here’s some practical advice (Slideshare below).


Here are some of the upcoming topics in the Stuck and Struggling series:

  • ADD Direction (company leaders who keep changing the compass)
  • Misplaced Persons (people in mis-matched roles)
  • Operational Vacuum (insufficient structure/process to enable growth)
  • Growth by Accretion (the tendency to take on new tasks and clients and people, without a clear plan)
  • Bad Clients/Wrong Clients (self-explanatory)
  • Inconsistent Revenue Model (something I and many others struggle with)
  • Broken Internal Communication (multi-faceted topic)
  • Commodity or Poorly Packaged Offerings (differentiation issues)
  • Scalable/Configurable vs. Custom Offerings (the craft-work, time-for-money trap)
  • Foggy Marketing/Messaging (failure to communicate clearly with clients and referrers)


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  1. Steve,
    I always feel like you are talking about me in these types of posts….
    Excellent insights and much appreciated.

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