Sometimes “it” is hard to name. The role hasn’t changed on paper, but something feels off. A new CEO arrives. A private equity or venture sponsor comes in. Decision-making speeds up – or sideways. Expectations shift, quietly.
This isn’t about performance reviews or onboarding missteps. It’s about whether your instincts are telling you you’re slightly out of sync with the system around you.
Use the questions below as a gut check.
Is the Purpose of Your Role Actually Clear?
When the role is vaguely defined, progress feels noisy instead of directional.
Many GCs believe they were hired to “fix legal,” while the CEO or Board is expecting something else entirely: a stabilizer, a deal enabler, a risk filter, or a decision accelerator. When that gap exists, frustration builds on both sides.
If you can’t clearly name the three outcomes that define success in this role right now, you may be operating without a shared target. Clarity creates momentum. Ambiguity creates motion without progress.
Whose Operating Tempo Are You Really Following?
Speed mismatches create friction long before anyone names them.
If you feel like you’re constantly “behind,” it may not be because you’re slow; it may be because no one ever defined what fast looks like. In sponsor-backed or high-growth environments, the standard is often directionally correct, not technically perfect.
Ask yourself: Do you know what needs escalation, what needs coverage, and what just requires a reasonable answer so the business can move forward? Legal judgment only works when it matches the company’s actual velocity.
Do You Understand How Power Really Moves in the Boardroom?
Boards aren’t presentation audiences. They’re influence systems.
If you’re treating board interactions as formal moments instead of ongoing relationships, you’re likely missing where decisions are actually shaped. Some directors test. Some steer. Some stay quiet but decide later.
If you’re unsure when to speak directly, when to advise privately, or how independence is expected to show up here, you may be operating without the full map.
Are You Valued for Output or Trusted for Judgment?
Volume can hide a deeper problem.
You can turn documents quickly, but you may still struggle if the right people don’t fully trust you yet. In senior legal roles, influence doesn’t just come from being correct; it comes more from having your input, advice, and counsel being sought.
Do business leaders bring you issues early, or only once positions are set? If trust isn’t there yet, prioritize credibility over throughput. A few visible wins matter more than a long list of completed tasks. One GC we know keeps a “win-list” developed and managed by his team.
Do You Actually Know Your Constraints?
Assumptions are expensive.
Many GCs expect to build, only to discover limits around budget, headcount, tech tools, or authority after decisions are already made or were made with the previous management team. When constraints arrive or stay implicit, legal becomes either a bottleneck or a runaway cost. Another GC tracks his actual budget against proposed outside counsel spend.
If you don’t have clarity on what you can approve, what needs permission, and where discretion actually lives, you’re likely making judgment calls on incomplete information.
Are You Embedded in Strategy or Reviewing It After the Fact?
Being adjacent to decisions isn’t the same as shaping them.
If legal shows up once the plan is mostly baked, the role becomes defensive by default. The real value of a GC is upstream helping frame risk, tradeoffs, and options before momentum locks in.
If you’re consistently reacting instead of shaping, that’s a positioning issue, not a capability issue. This concept was shared with us by a CEO looking to hire their first GC.
Do You Actually Understand the Culture or Just the Values Slide?
Culture is how disagreement is handled when it matters.
Every organization has rules that aren’t written: how pushback is received, how decisions really get made, and what happens when someone says “no.” GCs who miss this misread situations, not laws.
If you haven’t pressure-tested your read of the culture in real moments, you may be operating without a true license to influence. Or if the senior team has significantly changed are you in alignment with the new cultural norms?
Is Your Executive Presence Still Developing or Being Assumed?
For most of us, gravitas isn’t a trait, meaning it may not be innate. It’s a practiced skill.
Under pressure, people remember who was clear, calm, and proportionate. If feedback feels vague (“too detailed,” “too cautious,” “too sharp”), it’s worth taking seriously early before perceptions harden.
Executive presence improves with reps, feedback, and reflection. It doesn’t self-correct.
If several of these questions make you uncomfortable, that’s not a failure. It’s data.
Alignment drifts quietly – especially when leadership changes, capital arrives, or the business accelerates. The strongest or wisest GCs notice the drift early and recalibrate before it becomes visible to everyone else.
