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Holding a Mirror

What developing more than 40 people taught me about care, candour and growing leaders.

Darren Smith · · Design leadershipPart 2 of a series

One of the parts of leadership I enjoy most is developing people.

I like seeing someone recognise a strength they had been underplaying. I also value the harder conversation, when someone begins to understand what is standing between them and the next step in their career.

I believe in nurturing the people in my care. Whether we work together for a year or five, I want that time to mean something for their development.

That requires attention. It requires honesty. And it requires me to understand the person in front of me, rather than assume that everyone needs the same kind of encouragement.

During my time at Atlassian, I developed more than 40 people. Within my teams, I had the opportunity to grow five leaders. I also contributed to leadership development across the organisation.

The numbers give a sense of the scope. What interests me more is how that development happened, and what I learnt along the way.

Start with how they see themselves

A technique I used was to ask the team member and their manager to assess their level independently, before seeing each other’s assessment.

We worked against defined levels and dimensions. Each of us considered the accomplishments, behaviours and impact we had seen, then came together to discuss them.

I asked the team member to go first.

I wanted to hear their view of their contribution before my feedback shaped the conversation. What were they proud of? What did they believe demonstrated their level? Where did they think they were already operating at the next one?

There was often an interesting mix.

Some people inflated their impact. Others underplayed it. The same process needed to help both see their contribution more accurately.

That became a useful reminder for me: confidence and evidence don’t always arrive together.

Hold a mirror to what they cannot see

After hearing their assessment, I would share mine.

I thought of this as holding a mirror. There might be a strength they hadn’t recognised, a pattern they hadn’t noticed or a gap they were explaining away.

For someone underplaying their contribution, the conversation was about helping them see what their work had enabled. Who had benefited? What had changed? Where had their judgement helped the team move forward?

For someone overestimating it, we needed to examine the evidence more closely. What had they owned? What was the wider team’s contribution? How consistently had they demonstrated the behaviours they were describing?

That conversation needed care. Someone’s career matters deeply to them. But avoiding a difficult truth can leave them working towards a promotion without understanding what is actually required.

I also needed to remain open to what I had missed. An independent assessment only becomes useful if both people are willing to learn from the comparison. My view was a starting point for discussion, not something the team member had to accept without question.

Help people find their voice

Some of the people I worked with were capable, but lacked the confidence to make their voice heard. Helping them recognise their contribution was a starting point. They also needed opportunities to practise expressing it.

I started with resources like Toastmasters, giving people a platform to learn, practise speaking and become more comfortable sharing their thinking.

From there, I helped connect people with broader groups, including women in leadership communities, where they could learn alongside peers and be supported by people whose experiences felt more relatable to their own.

That mattered. I could offer feedback, encouragement and opportunities, but I couldn’t assume my perspective would meet every development need. Someone else might understand a challenge differently, or offer an example of leadership they could more readily see themselves in.

Part of caring for people is recognising where another person or community can support them better than you can. My role was to help make those connections and give people room to find a voice that felt like their own.

A spike is a signal. Sustained impact is the evidence.

One of the recurring conversations was about the difference between a strong moment and a sustained level of contribution.

An excellent project can show potential. A difficult stakeholder conversation can demonstrate growing influence. Taking the lead in an unfamiliar situation can reveal capability we hadn’t seen before.

Those moments matter. They give us something to build on.

But a one-off spike isn’t prolonged impact.

We needed to understand whether someone could demonstrate those behaviours consistently, across the scope expected at the level. Could they apply their judgement in different situations? Could others rely on that contribution over time?

Influence also needed to show up in the appropriate spheres. The expectations change as someone progresses: from their own work, to their team, to other teams and, where the level requires it, the broader organisation.

This helped make development more specific. We could identify the behaviour to strengthen, the opportunity to practise it and the evidence we would look for together.

Growing leaders means working with the gaps

I hired and developed leaders directly, as well as contributing to leadership advancement across the organisation.

One example was a leader who was excellent in people and practice. They brought real strength to those areas, but their contribution to strategy needed development.

That distinction mattered. A person can be highly capable and still have a gap that limits their readiness for the next level.

The conversation needed to make that gap clear without diminishing the strengths they already brought. We set development goals, and I provided support myself and through peers I connected them with.

I wanted them to have access to people who could extend their thinking and help them develop beyond what I alone could offer.

There is a responsibility here for the manager. Once we have identified a development area, we need to consider whether the person has a realistic opportunity to work on it. Feedback needs to lead somewhere.

There is a responsibility for the individual too. They need to engage with the feedback, seek support and practise the behaviours. Development is something we work on together.

Make room for different perspectives

My contribution to the emerging manager programme gave me another perspective on growing leaders.

I mentored senior individual contributors from across the business, including data science, programme management and design. It was a structured and candid introduction to leadership.

Working across disciplines reminded me how much context matters. People bring different experiences, strengths and assumptions to leadership. The conversation needs to start there.

It also reinforced the value of being honest about what the role asks of someone. Helping a person explore leadership includes helping them understand the responsibilities they are choosing, and where they will need to grow.

Build a practice that reaches beyond your team

I also sponsored the mentorship programme and designed its syllabus for a community of roughly 400–500 product designers, content designers and researchers.

That work connected individual development to organisational capability.

A strong manager can make a significant difference to someone’s career. I wanted us to create more ways for people to access support, perspectives and development opportunities across the organisation.

The programme gave us a structure for making that investment repeatable. Its reach was broader than my direct team, and its value depended on the people participating, mentoring and putting the learning into practice.

This is where my thinking about people, practice and strategy comes together.

People bring the capability. Practice gives us a way to develop and share it. Strategy helps us connect that investment to what the organisation needs to become capable of doing.

What I learnt

These approaches helped me grow careers, retain and motivate talent, and build a more deliberate investment in people.

They also sharpened my understanding of care.

Sometimes care means helping someone recognise how much they are already contributing. Sometimes it means being clear that their evidence doesn’t yet support the next level. In both cases, the conversation should leave them with a better understanding of where they stand and what they can do next.

I don’t want people leaving a development conversation trying to decode what I meant. I want them to understand my reasoning, be able to challenge it and have a practical path forward.

And I want to keep examining my own contribution. Have I made the expectations clear? Have I offered useful support? Have I helped create an opportunity, or simply described a gap?

Whether someone is in my team for a year or five, I want them to leave with greater capability and a clearer understanding of their own impact.

That is one of the most meaningful things I can contribute as a leader.

Who in your care needs a clearer mirror—and what will you do to help them grow from what they see?

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