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The Career You Can Only Explain Afterwards

Companion reading for the conversation with Simon Dudley.

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Nathan Coutinho began by studying accounting. Then a friend took him into a computer lab to see the web, and the plan acquired a fairly substantial hole.

He changed direction into management information systems, moved into consulting and eventually spent 17 years at CDW. His work took him through technical roles, corporate strategy and collaboration leadership before he joined Logitech.

Written down like that, it looks beautifully organised. Careers are very good at looking organised once someone has removed all the uncertainty from the story.

In our conversation for Before It Was Obvious, the more interesting pattern was Nathan's willingness to learn something he did not yet understand, then make it useful.

The assignment nobody puts on a vision board

One of his examples involved integrating product information between systems after an acquisition. There were part numbers, e-commerce requirements, images, warranties and all the other details that allow a business to sell an actual thing to an actual customer.

He did not particularly want the project. He did not arrive with the relevant expertise. It needed doing, and someone believed he could figure it out.

What he gained was a better understanding of the machinery and relationships with people he would work with for years afterwards.

That is difficult to capture in a career plan. The assignment may look like a detour. Later, it turns out to have supplied something important.

This is not an argument for accepting every unwanted job indefinitely. It is an argument for asking what you might learn, whom you might meet and whether the experience adds something your current role cannot.

Nathan's career kept giving him those opportunities because he became known as someone who could take an unfamiliar problem and produce a useful answer.

Knowing the technology is only part of the job

At CDW, technical experience eventually opened the door to corporate strategy. That meant learning unfamiliar subjects again, including financial statements and acquisition work.

Nathan also recalls being asked to explain cloud computing to the board. The significant part was what happened before the presentation. He expected to arrive, deliver his section and disappear. Instead, he was included in preparation with the wider leadership team.

They wanted a coherent account of the business. That required him to understand what others were saying and required them to understand his contribution.

It is an excellent example of development through access. A senior team can tell someone to think more strategically. Alternatively, it can let that person see how strategic decisions are discussed, questioned and explained.

The second approach provides rather more to work with.

A technology shift turns into a billing problem

Our discussion of cloud also exposes something easily missed in technology commentary.

The interesting question for a reseller was not simply whether customers would move towards subscriptions. It was how the company would operate when they did.

Nathan describes the work involved in adapting billing systems and dealing with different supplier platforms. A new commercial model had to be made compatible with a business already built to transact in another way.

The product announcement is the visible bit. The operational change determines whether the business can deliver it.

That distinction matters whenever a market changes. Understanding the technology is necessary. Understanding which processes must change around it can be where the harder work starts.

Three words that annoyed him enormously

When Nathan joined Logitech, I told him to “do good things.”

He had expected a clearer brief. Having left a structured environment and a substantial leadership role, he was understandably unimpressed by my contribution to the onboarding process.

Eventually, that freedom helped him find where he could add value. It also came with work: speaking to people across the organisation, understanding regional differences and learning how the company operated before deciding what to build.

But this is where the story needs a little honesty from the manager.

I have given similar freedom to people who needed much more structure. In some cases, I failed to provide the defined role and expectations they required. That was my failing as a leader.

Different people need different conditions to do good work. A company needs people who can define a new problem and people who can execute a well-understood process. Often, it needs someone who can do both.

The clever bit is recognising what the work requires and what the person needs. Repeating the same management slogan to everyone is considerably easier.

Learn enough to ask a better question

Nathan now applies the same curiosity to filmmaking. He is learning the craft: shooting, editing, pacing and colour grading.

The value extends beyond making a video himself. When you understand how the work is done, you can brief someone else more clearly, assess their proposal and recognise when a simple change has acquired an implausible price or timescale.

You do not need to become the world's best editor. You need enough understanding to have an informed conversation with one.

For managers, that is a useful distinction. Delegation does not remove the value of knowing what you are asking for.

The slides come last

Nathan's first presentation lesson was especially memorable. He delivered 150 slides in 40 minutes and thought he had done brilliantly. A colleague pointed out that members of the audience had been falling asleep or leaving.

He had measured his performance by the content delivered. The audience had experienced something else entirely.

Practice and coaching changed his approach. He learned to move with purpose, read the room and build a narrative before assembling the deck.

We agreed on the final test: know the subject well enough to keep going when the slides or notes fail.

Across the conversation, the pattern is consistent. Curiosity creates the opportunity to learn. Doing the work turns that interest into capability. Communication helps other people see why it matters.

That is a fairly useful career strategy, even if it takes years to explain how the pieces fit.

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