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A question of Leadership

Melissa Rosenthal Melissa Rosenthal

When a Judgment Problem Looks Like a Knowledge Problem

There's a particular kind of discomfort circulating in senior leadership right now that doesn't get named very often.

It's not confusion about AI exactly, though that's part of it. It's the vulnerability of being expected to lead clearly through something you're still working out yourself, in real time, in front of people who may understand aspects of the technology better than you do.

The conversation about AI is loud, and most senior leaders are in it, at least visibly. They're attending briefings, sitting through demonstrations, forwarding articles, asking their teams what they're doing with it and, increasingly, experimenting themselves.

I've spoken with executives who have started generating code, building simple applications or creating AI workflows, despite having no particular technical background. Sometimes that's driven by genuine curiosity and a desire to understand the technology first-hand.

Sometimes I find myself wondering whether something else is going on, whether there's an unspoken belief that leaders need to prove they "get it" before they're allowed to lead through it.

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Melissa Rosenthal Melissa Rosenthal

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”.

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Melissa Rosenthal Melissa Rosenthal

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.

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