Insights
Confirmation, not advice: what members actually say the group gives them
By the second session, something had shifted, and it wasn’t the advice. It was the questions.
Leo Judkins, Founder, The iGaming Leader · September 2026
One of our members almost quit after her first session.
She called the person who’d referred her and said, plainly, this isn’t for me. The conversations felt like they were going round in circles, and the advice people were offering was stuff she’d already tried. She’d joined wanting to hear something new, and on that first call, she didn’t feel like she had.
By the second session, something had shifted, and it wasn’t the advice. It was the questions.
What changed, in her own words
She’d been in the middle of a brutal stretch: replacing a CTO, letting go of a head of finance she’d struggled with for a year and a half, making a hard call on her account management structure. All decisions she’d been circling in her own head for months, decisions that, as a CEO, nobody internally was really positioned to challenge or validate, because she answers to no one but herself.
Six weeks later, all three had actually happened. Not because the group told her what to do. Because being asked pointed, specific questions, week after week, forced her thinking into a different shape than it took when it was just going round and round in her own head, alone, at whatever hour she happened to be awake wrestling with it.
Her own description of it: the satisfaction was 40% from what she received and 60% from what she gave. Explaining her own hard-won lessons to another member going through a nearly identical challenge, one step behind her, turned out to matter as much to her as the input she got on her own situation.
And the biggest, most unexpected outcome wasn’t any single decision. It was confidence, specifically the kind she hadn’t realised she was missing: not confidence in making a decision, but confidence in not relitigating it in her head for weeks afterward. As she put it herself, the six weeks gave her a confirmation that she was confident in what she said, what she did, what she thought, in her own decisions. Not because anyone handed her that confidence. Because she got it back through giving advice to others that they actually took and acted on.
Why “confirmation” is the more accurate word than “advice”
This is worth pausing on, because it cuts against how most people imagine a mastermind works. The value isn’t a room of smart people telling you what to do. Most senior executives already know, at some level, what the right move is. The paralysis isn’t a knowledge gap. It’s the absence of anyone with the standing and the distance to make that half-formed decision feel real enough to actually execute.
That’s what “the value was accountability and challenging questions, not advice” actually means in practice. Nobody handed her the org chart. The questions did the work advice can’t: they took a decision that existed only in her own head, turned it over from several angles she hadn’t considered, and by the end of it the decision felt like something solid enough to act on, rather than something she was still turning over at 2am.
Why this only works with real preparation and real stakes
This isn’t a passive process. She took the hour seriously enough to prepare for it, sometimes fifteen minutes beforehand, sometimes an hour, because she felt a responsibility to the other people in the room who were doing the same for her. That mutual seriousness is what makes the questions sharp enough to be useful. A group where people show up unprepared, or without real stakes on the table, produces exactly the surface-level advice-swapping she nearly walked away from after the first week.
It’s also worth being honest that pushing through that first uncomfortable session mattered. The instinct to bail after one disappointing call is completely normal. The value, in this case, only showed up on the other side of continuing anyway.
Where this changes
Nobody in the Inner Circles is there to give you the answer. They’re there to ask the questions that turn a decision you’ve half-made into one you can actually stand behind, and to notice when you’ve stopped relitigating it.
See how the Inner Circles workQuestions this usually raises
What do members actually get out of a peer advisory group like this?
Not advice in the traditional sense. Members consistently describe it as confirmation, the confidence to act on a decision they’d already half-made, and to stop relitigating it afterward, built through structured questioning rather than being told what to do.
Why do challenging questions work better than direct advice?
Because senior executives usually already know the right move at some level. What’s missing isn’t information, it’s a structured, credible process that turns a half-formed decision into one they trust enough to actually execute.
What if the first session doesn’t feel valuable?
That’s common. The value tends to build over the first few sessions as trust and preparation deepen, and several members who nearly walked away early on describe the shift happening specifically in session two or three.
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