1 Habit The Most Successful People In Tech Have In Common

Mitch Malone
3 min readMay 14, 2024

All of the best people in the business of technology exhibit a variety of habits and skills that make them good at what they do depending on their specialization. In general, top tier tech people specialize in a single skill and then have other skills which surround and support that. We call this being T-shaped.

This is an expected set of qualities to be in the top 10%, but if you want to be in the top 10% of that group then the game changes a little.

The thing I see, again and again, separating the good from the exceptional in tech is the skill of managing expectations. Top performers know how to set and achieve goals, and even more importantly they know how to effectively manage expectations when dealing with stakeholders.

When managing expectations you can never truly control how a change might be perceived, but you you can control being rational and honest with updates, and being clear with stakeholders about what you are going to achieve.

All of the best people I’ve worked with call out issues early, offer options for moving forward, and own up to changes in deadlines or strategies.

Flipping It

Picture this — you’re a stakeholder inside a business and you’re aware that there are some deliverables schedule by your team for the end of year. Teams are under some pressure to deliver and they’re justifiably a little vocal about it, but ultimately they’re showing up every day and working hard.

You’re proud of the team and you’re excited to see the results.

Now imagine the frustration as the end of year deadline comes and goes without the delerables being met. You knew that it was going to be tight, but at no point was it made clear the deadline wouldn’t be met, and naturally you’re frustrated.

Not all conversations about changing deadlines or deliverables are going to be met with enthusiasm. But not having the conversation early enough is always a worse option, and it’s important to resist the urge to just put your head down and hope things go well for your deadline.

Being Aware of Issues Early

The first step of improving your stakeholder management skills is being aware of issues early enough to be effective. This means keeping a close eye on project deliverables and progress and always having a strong awareness of your status.

You can’t call out issues if you’re blind to them yourself.

At least a few times a week you should step outside your daily grind of getting stuff done and assess the status of the project(s) objectively. When working on a project you are always the most knowledgeable person on it’s progress and likelihood of delivery.

Having the Conversation

It’s not enough to call a meeting and spill the bad news. This is a terrific start, but if you’re aiming to ensure the conversation goes well and you’re still driving great outcomes you need to do better. The key here is to bring options and recommendations.

Perhaps there is a small change of scope that will allow a deadline to be met. Perhaps features are too complex for your teams current capacity and a simplification is in order.

At the end of the day the objective is clear; along with the update on project status needs to come strategies and options in order to move forward.

Be Early

If you’re not early, you’re late. The best time to have the conversation about problems is when they are discovered. Provided you’re staying keenly aware of challenges ahead, it should be easy to have these conversations early and that is the best time to have them.

There is little point in bringing bad news when it’s already too late to change course or apply learnings.

Wrapping Up

No one ever wants to have these conversations. It never gets easy to disappoint stakeholders and there are times when the barrier between project contributor and stakeholder feels overwhelming.

However, it’s essential to remember that without clear communication and managing expectations, a project can quickly veer off course. It’s not about failure, but about adaptability and proactive problem-solving. This is the habit that truly differentiates the successful from the rest in the tech world.

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Mitch Malone

Product and engineering leader (prev. CTO @ Linktree, Head of Eng @ BlueChilli). Nomad, remote worker, writer, photographer.