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A question of Leadership
Executive Judgment in Unfamiliar Systems
The fine line between solving problems and misreading the context
In the first weeks of a new senior role, things can feel awkward and unnatural.
Our decision-making feels clunky. We’re missing knowledge of the customs and processes that enable us to move at speed. At the same time, we see early signs that things could be clearer, faster, and more effective. Our instinct is to act to demonstrate capability, reinforce the hiring decision and gain confidence.
The problem is, we don’t know what we’re missing. We don't know what the organisation is optimising for, which inefficiencies are deliberate trade-offs and which are consequences of previous decisions, why previous attempts to change things have broken down or how decisions get made when the pressure is real.
It’s tempting to rely on our track record, reference past successes and draw parallels when making recommendations. Track record might be why we were hired, but once inside a new organisation, that history carries very little weight. “Show me what you can do here” is much more prevalent than “tell me what you’ve done elsewhere”.
What if you’ve already formed the wrong picture?
A client arrived at a recent coaching session with a noticeably different level of positive energy. Turns out, 48 hours earlier, she had resigned from her current role, having just accepted another senior role at an alliance partner. The new role is within the same industry, and she'll be working with people she "knew by reputation".
It had taken no time at all for the word to get out that she was joining the new organisation. Her connections began reaching out immediately with unsolicited, well-meaning opinions. Recommendations to align with certain people and to watch out for others. Information about where hidden tensions were likely to impact her new responsibilities. A heads up on what she is walking into. By the time we spoke, she had formed a detailed picture and had already started shaping her approach in response.
I asked her one question: how do you know you can rely on that information?
I knew by the pause that followed I'd hit a nerve.
You don’t have to be right to be helpful
As leaders, we’re involved in many conversations where our role is clear. The Board wants a recommendation, an investor wants an outcome, or the regulator wants an answer. We spend years building expertise to deliver those expectations. Those skills are real and valuable. In reality, most of our week doesn’t look or feel like that. It’s usually messier: strategy still forming, unclear problems emerge, forcing our teams and us to consider something new. In those conversations, the same frame that serves us in the boardroom can (quietly) work against us.
It’s not about having the answer.
Clarity is the end, not the beginning
The one place you don’t have to have the answer
At every level of leadership, there is an unspoken expectation: you are the person who brings clarity to the room.
Others come to us with problems, half-formed ideas, competing priorities. Our job is to receive all of that and return something useful, perhaps a direction, a decision, a pathway through. We do this all day, in every meeting, every conversation.
Which makes it harder to admit, or even recognise, that our own thinking is sometimes just as unresolved.
“Sorry, I’m a bit scattered today.”
“I’m jumping around all over the place.”
These are among the most consistent opening patterns in coaching sessions. Leaders join, take a breath, and apologise for the state of their thinking before they’ve said anything of substance.
Progress Over Perfection. Is it helping or hurting your team?
Last night I ran a coaching session with a group of cross-functional leaders.
We were talking about the relationship between priority and capacity, and the temptation to blame inadequate capacity, when the problem often stems from unclear or undisciplined prioritisation.
The conversation turned to perfectionism and how it constrains capacity.
"We keep telling people to focus on progress over perfection, but then we all get judged when the work isn’t right”.
The group went quiet. They’d all said some version of it to their people. Test and learn. Done is better than perfect. Ship it.
These aren't careless leaders. Most quietly admit to perfectionist tendencies. It’s not about lowering the bar. It’s about freeing their teams from paralysis. A perfectly reasonable leadership lever when you’ve got big goals and limited resources.
Perfectionism, when it's unchecked, is expensive. It slows execution and increases anxiety. It turns leaders into bottlenecks. When accuracy genuinely matters, the instinct to get it right forms the DNA of individuals and the team. For senior leaders, it becomes more complicated as pace, learning and commerciality form part of their decision criteria.
Why does attention feel so rare?
When was the last time someone thanked you for paying attention to them?
Not for solving their problem or making a decision or moving things forward - just for being fully present. For not paying partial attention while monitoring Slack. Or splitting your attention between them and your mental to-do list. Complete, undivided, you-are-all-that-matters-right-now attention.
If you're drawing a blank, you're not alone. And if someone has thanked you recently, I wonder what it says about us when our presence has become remarkable enough to name?
A Question of Context: Why Good Leaders Struggle
You know that leader who seems like they tick every box? Clear vision and values, results-oriented, while balancing genuine care for their people. But somehow, they can't gain traction even though they seem to be working incredibly hard.
It’s likely to be a context problem.
I've been thinking about this as I’ve watched talented, thoughtful leaders exhaust themselves trying to lead with purpose and values in organisations that prioritise something different. They're not failing because they're doing it wrong. They're struggling because there's a fundamental mismatch.
Leadership success requires alignment between your values and style, role requirements, and organisational culture.
Why first team commitments don’t stick
Picture this...You're heading into a retreat designed to transform your newly formed leadership team into a true 'first team.
When you think about your 'first team', who comes to mind?
Is it the team you lead, your function, and your direct reports? Or is it the team you're a member of?
The most common response from coaching clients is the team that they lead. The problem with that, according to Patrick Lencioni in his work on Organisational Health, is that when the leadership team comes together, conversations are focused on lobbying and jockeying for power rather than making decisions in the best interest of the organisation. And it leaves functional teams arguing with each other over priorities.