He Who Hesitates Is Lost
- Hilltop Marketing

- Aug 22
- 2 min read
Updated: Sep 5

Great marketing happens when professionals are empowered with ownership, flexibility, and courage to innovate – all driven by an innate passion to “move the needle.” A sure-fire way to stall progress is when non-marketing leaders undermine that expertise through second-guessing, indecision, or micromanagement.
What do we mean by non-marketing leaders? For tech startups, this is usually the CEO/Founder who’s an experienced software developer. In larger organizations, this could be a sales leader, engineering head, or even a finance or legal exec.
All of them have experience working with marketing professionals, but for a few exceptions, none of them have actually run marketing. Despite this, whether driven by ego or high intelligence, many of them believe they know marketing, including: AR, PR, product marketing, etc., better than those who actually do it daily.
And that’s where trouble starts. Questions and challenges are good. They keep marketing professionals focused and strategic. However, when everything is questioned – every message, every piece of collateral, every campaign element, every decision – this kills good marketing; worse it kills marketing teams’ passion, inspiration and dedication.
Here’s a condensed, real-life example of what this can look like:
Startup CEO: Why am I doing all these analyst briefings? Six per quarter is too many.
Marketing Pro: Because we’re not a client with any analyst firms, we have no visibility into upcoming reports. The risk is, if a report comes out and we are not included, it would be highly detrimental. So it’s important that we regularly brief analysts to build a relationship.
Startup CEO: Why am I only briefing three analysts per quarter?
Marketing Pro: Because you objected to briefing multiple analysts, we cut it in half. Let’s agree to focus on securing three briefings per quarter with the most influential ones.
Analyst report comes out, startup not included.
Startup CEO: Why weren’t we included in this report? This is a huge fail!
Marketing Pro: Because we don’t pay for any analyst services, a briefing becomes optional for them. This firm was not on our three targets for this quarter.
Startup CEO: We need to start briefing a whole lot more analysts, immediately!
Marketing Pro: On it.
Here, the CEO didn’t see anything immediately tangible resulting from the briefings. For that reason, he believed analyst briefings, “are a waste of time,” leading to a classic example of leadership vacillation.
“Questions at every turn become roadblocks”
Vacillation leads to wasted time and energy. Questioning everything erodes trust. Chasing shiny objects creates never-ending urgencies, and when everything is urgent, nothing is.
What non-marketing leaders need to know is that second-guessing everything, micro-managing the mundane, and constantly changing decisions results in contempt, stagnation, and eventually, talent departure. The inability for leadership to stay committed to a plan creates hesitation. And as everyone knows, “he who hesitates is lost.”


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