You’re Allowed to Ask for Help With This

At some point, something changed.

Maybe it was a high-profile incident where your company put you out front to answer for decisions you didn’t make. Maybe it was after months of trying to rebuild trust with cross-functional peers who still associate you with your predecessor’s reputation. Sometimes it’s quieter than that, a conversation with yourself on a Sunday night where you honestly don’t know if you want to keep doing this job or feel overwhelmed, exhausted, or disconnected.

Whatever the moment was, you probably still showed up, stayed composed, and said the right things to the right people. But you probably didn’t figure out what you’d need next or who you should ask.

Over time, I’ve learned to recognize the shape of these conversations before they begin. For example, a CISO sitting across from me, three weeks after their company used them as the public face of a breach they didn’t cause, trying to figure out how to talk about what happened without sounding either defensive or broken. Or all the times people told me they don’t know if they want to keep doing this job. There’ve been new CISOs trying to repair relationships with every cross-functional peer their predecessor torched, carrying the weight of damage they didn’t create; and fearful statements like, “I think what they’re doing might be illegal, and I don’t know what to say to anyone.”

I’ve had versions of all of these conversations. They require something different from the craft skills that got me into the room and they’re worth talking about directly.

The unique difficulty of your role

CISOs operate in a structural isolation that most people outside the function don’t fully appreciate. You’re accountable for outcomes you often don’t control, expected to be the steady presence in a crisis regardless of whether you caused it or warned it was coming, and you’re frequently the most technically credible person in a room full of people who are nonetheless empowered to override you. And when something goes wrong, you’re often the most convenient face to put on it.

Being sacrificed as the public representative of an organizational failure is a distinct professional experience. It’s not the same as being held accountable for something you actually did; it involves being asked to absorb consequences on behalf of a system and then continue operating in that system as if nothing happened. The communications challenge on the other side of that experience, e.g., how you talk about your tenure, your decisions, your value, and your next move, is genuinely hard. It goes well beyond talking points and requires working through what you actually believe about what happened before you can credibly say anything about it to anyone else.

Walking into a role and discovering that your predecessor burned every relationship you need to do your job is not a simple messaging problem, either. That’s a trust deficit you’re being asked to repay on someone else’s debt. The work of rebuilding those relationships is fundamentally a communications problem covering how you show up, what you acknowledge, what you don’t, how you sequence the conversations, and how you establish your own credibility without throwing someone else under the bus. Strategy and interpersonal efforts have to work together, and getting either one wrong makes the other one even harder.

Naming what you’re experiencing matters

There’s a reason a lot of CISOs in difficult transitions don’t ask for help clearly: the instinct is to frame everything as a strategic or operational problem, because that feels more solvable and more professional than saying “I’m not sure I trust my own judgment right now” or “I’m exhausted in a way that isn’t going away.” Recognizing these feelings can help you build trust with yourself and others, which is essential for effective support.

But the framing you use to describe your situation determines the kind of help you’re able to receive, which means the first and most useful thing you can do is slow down before you hire anyone, brief anyone, or start working on your narrative. Ask what you’re actually trying to figure out. Is it what to say, or whether you believe it? Is it how to repair a relationship, or whether it’s worth repairing? Is it how to position your next role, or whether you want a next role that looks like this one?

Those questions change the work. And they’re the ones worth answering before anything else.

What good communications help looks like 

It doesn’t start with messaging. It starts with someone asking you the questions above and taking the answers seriously.

From there, the work looks different depending on where you are. If you’re coming out of a situation where you were put in front of regulators or policymakers to answer for something systemic, the goal is language for a complicated professional history that is honest without being self-destructive. Instead, it’s accurate, credible, and constructed in a way that preserves your ability to do the next thing. If you’re inheriting a damaged environment, it’s about sequencing the relationship repair conversations, knowing what to acknowledge versus what to leave alone, and building credibility without making the underlying situation worse. If you’re trying to figure out what you actually want to say about your career going forward — on panels, in interviews, in the rooms that matter — it’s about finding what you’ve genuinely learned rather than what you think sounds best.

And if the question underneath everything else is whether you want to keep doing this job, that deserves a real answer before you invest in any narrative work at all. The narrative you build should be in service of something you actually want.

A specific note on whistleblowing

If you’re sitting with information about illegal or seriously unethical practices at your organization and trying to figure out what to say and to whom, the communications dimension is real, but it comes later. Before you work on how to say it, you need to understand your legal protections, your exposure, and your options. Talk to an attorney before you talk to anyone else. The communications strategy follows once you know what you’re actually trying to accomplish and what the realistic outcomes are. Trying to message your way through a situation you don’t yet have legal clarity on is how people make it worse.

The ask you’re probably not making

Most CISOs in difficult situations put their team first. Not always effectively, but consistently, meaning the effort, energy, and political capital they do have go toward fighting for resources, pushing back on unreasonable timelines, and making the case for their programs. Their own situation gets whatever is left over (if anything).

If you’re in one of the situations this post describes, the most useful thing you can do right now is resist the instinct to reframe it as something more manageable than it is. Name it accurately — to yourself first, and then to whoever you bring in to help. The quality of the help you get will follow directly from the honesty of that conversation.