Photo by Michael Schreiber on Unsplash

Turning things around

A moment of reflection & appreciation in leadership

Jezz Santos
5 min readJan 22, 2025

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I’ve been having a pretty tough time at work helping a B2B SaaS business turn the ship around, and bringing everyone on that journey, at the same time, doing a bunch of “earth works” to reset the foundations for the future. Not fun, at times, but at some point very rewarding in brief glimpses.

If you know much about small/med organizations that means bringing everyone on the journey, from the CEO to the Board to everyone at the coalface, whether that’s inside your sphere of influence, or whether that’s some people outside it. It’s not inclusive of everyone in the company, but it sure is larger than just “who reports to you”.

To make that picture more fun, in a product company (where I am doing this work), the” product unit”, which I lead, is at gravitational center of the company. All other departments of the company have a direct dependency on this team, and are directly impacted by what this team does, whether you like it or not.

Sales, Success, Support, Marketing, Finance you name it. They all depend on the things the product team does. And this is why most product companies are very challenging places to work, and notoriously hard to turn around. Especially, when they are not even “seen” as the center of the company!

There are many challenges in being a Product Leader of a company like this. For my style of leadership, those challenges mostly revolve around communications and alignment in what to focus on, what’s important, and how to stay focused on it. This is my 7th startup, so I have some experience of these things, not just in startups but also as a consultant (in a past life) at organizations of all sizes and scale, struggling the same ways.

Being a “systems thinker” helps a great deal in this kind of work. In fact, I’d say its just about mandatory, to do this well. I can’t see how you could this kind of thing otherwise. Perhaps with generous gifts from God, or perhaps a great mentor behind you telling you how to take each step and interpret every clue — but not likely, in my estimation.

If you don’t know how to recognize and trace the causes and far reaching effects in a company, of things like: lacking leadership, lacking management, lacking effective processes, lacking people skills, thus lacking collaboration, low trust and maligned mindsets and misplaced competition - then I don’t think you stand a chance of making much of a difference for this kind of change. All those things are generally, and simply, self-inflicted root causes (created by the people already at the org, or recently gone) that are barriers to making change at the organization level. If you can’t identify them and address them directly, then how do you get anyone to care enough about them to fix them themselves?

You certainly can’t do that for them! Trust me, that certainly does not sustain for long! Try to learn from those who have failed at trying that several times, past!

Now, I don’t claim to be the best communicator in the world, I work with, and have worked with, far more skilled communicators to know this about myself. But I do care deeply about treating people well, and addressing their in-built purpose motives to get the results we all care about.

Sadly, many people in leadership positions in many companies don’t get this truth about the people they work with, favoring more of the, shall we say, Edwardian motivators to deal to the bad things they see and experience with those people — go figure! It’s more common than you might think.

A rare moment

Photo by NARINDER PAL on Unsplash

One of the advantages of being the kind of product leader that I am, (I still have no precise categorization for it — except for something whimsical like “compassionate” or “empowering”) is that in a product unit of only 10 people, there can be many team members making individual decisions, important design decisions, all at the same time. All communicating them to the rest of the team, at the same time, all clarifying, qualifying, quantifying, recruiting input, and resolving them all at the same time, in real-time, in parallel!

Today, I had a brief moment of clarity, related to this.

If this is happening around you in slack for example, its possibly pretty interesting/cool to observe, or its terrifying to some perhaps?

Now you get to choose how you react to this.

Do you need to respond?

How should you respond?

If you are the kind of leader who thinks its your job to have all the answers and make the calls, and pursues control of every decision that all those people are making without your immediate input. Then you might have heightened anxiety levels everyday knowing that you have to keep on top of all of it and have your say, and must help them make the ‘right’ decision. Or you might feel it your decision to make for them, and they are simply signaling that they waiting for you to make that decision for them. Well, I feel very bad for you, and for them, because its likely not to continue this way for very long, if at all. You may never see this happening this way.

If you are the kind of leader, that feels at ease that your people are best placed to make these decisions themselves, since they have all the things they need to do that (or can get them if they need them), and you trust them to come to you only if they are missing critical information to make those decisions. Then like me, you probably see the awesomeness in all this, and you would be demonstrating that gratefulness to them, at some point.

There is nothing quite like the delight of being aligned with those people you trust to do what is right for the business — when you are not around, and ironically, even when you are around — its a truly beautiful and wonderous thing!

GO you good people you!

p.s. This is by design, it is not a bug!

BTW: If are liking this idea, and thinking “oh boy, I’d love to have more of that where I work”, and you don’t know what it takes to get there. Then, I can assure you, these moments come infrequently and fleetingly, because the rest of the time, you are doing all the ground-work with those people to make sure they are very informed, comfortable and very safe doing these things without you as a bottleneck in their way — even when you are around and available!

Hit me up if you want to know what those things are, you might be surprised!

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Jezz Santos
Jezz Santos

Written by Jezz Santos

Growing people, building high-performance teams, and discovering tech products. Skydiving in the “big blue” office, long pitches on granite, and wood shavings.

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