Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Read MoreThe leader's job isn't to have the answer. It's to create conditions where the best answer can emerge. That means encouraging disagreement without punishment. Creating opportunities for information to move across functions. Making it safe for people to challenge assumptions, including your own. The highest-performing teams in these simulations don't succeed because they have the smartest leader. They succeed because nobody in the room is waiting for one person to have all the answers.
Read MoreHere’s what I’ve noticed about the leaders who wait. They’re not unaware. They’re not ignoring obvious problems. They see them. They just learn to live with them. Margins tightening a little each quarter. A team dynamic that feels slightly off. A process that’s inefficient, but still works. None of it is broken enough to force action. So it waits. And while it waits, it becomes the new normal.
Read MoreYou can pull data instantly, generate a strategy in seconds, and pressure-test your thinking with something that sounds confident and coherent. And still walk away with the exact conclusion you started with. Not because the tools are broken. Because they're flexible. Give ten leaders the same data and they'll reach ten different conclusions. Give them AI, and each one can explain why they're right.
Read MoreEmotionally, walking away from a past loss feels worse than risking a future one. Psychologists call this loss aversion. People feel losses more intensely than equivalent gains. A million-dollar loss feels catastrophic in a way a potential million-dollar gain never will. That is why leaders keep pouring resources into failing projects.
Read MoreEntrepreneurs who build traction almost always skew urgent. That urgency is often what gets the company off the ground in the first place. At scale, that same instinct becomes disruptive. People struggle to understand priorities. Context switches constantly. Everything sounds like a crisis. Leaders start mistaking urgency for accountability and patience for disengagement. So founders hire someone to "balance" them. Often a COO, Chief of Staff, or operations leader who skews more patient. In theory, it's a purposeful pairing. In practice, it creates conflict.
Read MoreMany leaders do the same thing with every hard decision. If you’re waiting for the right time, you’ll never act. There is no perfect information. There is no risk-free moment. There is no version of this that doesn’t require courage. Make the decision. Or don’t. But stop pretending indecision is neutral.
Read MoreMost leaders don't call themselves perfectionists. They say they're being thorough. Setting the bar high. Still working to get it right. That's not always what's happening. Perfectionism rises as uncertainty rises. When leaders feel watched, judged, or exposed, perfection becomes the shield they grab.
Read MoreWhen you waffle, you're not avoiding a choice. You're making one. You're choosing to stay stuck. You're choosing to slow your team. You're choosing to let opportunities expire. Most of the time, the facts that informed your original decision haven't changed. Only your emotions have. Make the decision or don't. Stop pretending indecision is neutral.
Startups and Small Businesses sometimes find themselves at the edge of a chasm. With success in developing and growing their business, a stage is reached where they find that the "next step" is a big one! Trajectify partners with the entrepreneur to build momentum and trajectory to be able to cross the chasm.
We offer private and group (Mastermind) coaching and hold frequent events and seminars.
Trajectify is founded my Mike Krupit, veteran of eight startups. Mike has helped dozens of companies grow and mentored and advised hundreds more.
Most founders and executives I work with are uncomfortable talking about how they look. It feels shallow. Not the point. I get it. They started their companies because of a vision, not an ego. By the time they're working with an advisor, they're wrestling with real problems: who belongs in which seats, how to build accountability, how to run a leadership meeting. Thinking about personal image can feel self-indulgent by comparison.
Founders tend to think about a major transition as a singular event. You prepare, announce, close, and now you're a different company. In my experience, the company starts changing well before any of that happens. I've been through this several times now, and the details were different every time. The weirdness was pretty consistent.
Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Ask a room of leaders why they set goals and most will say accountability. That answer creates the problem. Goals exist for alignment. The company needs to reach a number, so this group does this, that group does that, and together the math works. Everyone is pointed in the same direction. Focus comes second. A good goal tells you what to say no to.
The instinct to build a team that moved in the same direction, at the same pace, with the same set of perspectives is limiting. Consistency is created at the expense of range. The goal isn't alignment of strengths. It's coverage. The most dangerous teams I've seen weren't the ones with conflict. hey were the ones with none. Where every conversation ends in agreement. Where nothing gets surfaced. Where the people who see things differently may have learned to stop saying so.
The same restlessness that makes it hard to stay on plan is what made them start the company in the first place. The wandering mind, the refusal to be satisfied with what already exists, the ability to see something before it exists: that's not a disorder. That's the source.
If you're building a company, knowing your role isn't optional. The visionary needs someone who will build what they see without getting in the way of the seeing. The integrator needs someone who will point at the moon and mean it and keep pointing at the same moon long enough for the bridge to get built. The mistake I see most often: trying to be both or hiring someone who mirrors you when you need someone who complements you.
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I don't think every CEO needs to become a LinkedIn personality. The question is simpler. Who needs to know you exist? Where are they? And what would help them understand how you think before they ever sit across from you? That answer will change as the company grows, as your buyers change, as platforms come and go. You adjust. That I don’t think you can do anymore is decide visibility isn’t part of your job at all. Your personal brand is important to your company’s brand.