“Can I Interest You in Some Dessert?”: How Strategic Advisors Maximize Value and Leave Nothing On The Table

Consider this: The best waiters never wait for YOU to ask about dessert. They lean in halfway through your entree and ask if you’re saving room for the fancy cake they are known for. Now you can't stop thinking about it.

You may have told them you were coming in to try the chef’s famous Baked Alaska, but they know you’d be missing out if you didn’t also try their reputable dessert.

As a marketing strategist, I’m still learning the art of, “Can I interest you in some dessert?” Always having the next idea ready, even before the client asks for it. Looking out for what they don’t know they need.

That's not upselling. That's strategic advisory.

What separates strategic advisory from order-taking?

Most of us started our journeys by selling what was in front of us. A deliverable, a project, a fixed scope. Selling strategy means selling something less certain. It means staying in the conversation long after the contract is signed.

If you’re anything like me, that feels risky. Like naming a need the client hasn't asked about yet is arrogant, or even offensive.

But staying quiet about it isn't humility. It's a missed opportunity to serve them at the level they actually need. Nobody leaves dinner grateful they weren't told about the soufflé. But they might leave wishing someone had mentioned it before the check came.

A client tells us what they think they need. We hear it, we scope it, we deliver it. What we don't always do is stop and ask whether that first answer was the whole picture.

Most of the time, it isn't. Growth usually requires more than a client can name at the outset.

Sometimes that's because they don't know what's possible yet. Sometimes naming the real scope feels too big to say out loud, even to themselves.

Either way, if we take the first answer at face value, we cap our work at the level they asked for. Not the level they're actually capable of reaching.

Staying curious after a client thinks they've already told you everything is the actual job.

What happens when you take the first answer at face value?

We were recently referred a client for messaging work and a keynote. Their organization was at a turning point, and how they talked about themselves needed to catch up to where they were headed.

At the start, we asked the obvious question. “What's the state of your brand?”

They told us it was simple but sufficient. Fine as is. We took that answer at face value and moved on.

Looking back, we shouldn't have. We should have explored it instead of just accepting it. We should have gotten more curious.

Months later, we got to the keynote work and needed their logo files and brand guidelines. What we got back told a different story than the one they had given us at the start. The files were outdated and barely usable.

We said so directly. “If this is everything you have, we'll need to rebuild it from scratch. And honestly, your brand is due for an update. Would you want to refresh it while we're in there?”

They said yes. That conversation turned into a full rebrand. 

Where does the next need actually come from?

Once the rebrand started, we sent the client a discovery questionnaire. Somewhere in answering it, they realized something they'd never said out loud before. Their name didn't match who they were becoming anymore.

Nobody had raised that at the beginning. Not because it wasn't true. Because nobody had asked the question that would surface it.

That's the pattern worth noticing. We didn't pitch a rebrand or a rename to this client from the start. We asked good questions, stayed present in the work, and the real need showed up on its own.

The menu isn't something you invent. It's something you uncover, one honest question at a time.

Trust is what turns scope expansion into partnership, not a pitch

Nobody walks into a dental  appointment hoping to hear they need more work than they planned for. A good dentist still has to say it. Whether that lands as a violation of trust or as genuine care depends on the relationship already in the room.

With the aforementioned client, these conversations were never contentious. They were collaborative, because we'd built the kind of trust where expanding scope felt like partnership instead of a pitch.

Part of that was them. This client’s team are good communicators, and that made every one of these conversations easier to have.

But part of it was us. We showed up curious instead of certain, honest about what we'd missed instead of covering for it. That's what earned the room to keep asking.

That doesn't happen by accident. It happens because we stayed curious instead of defensive, and direct instead of pushy.

For those of us who came up doing deliverables work, admitting a client needs more than we quoted can feel like failure. It isn't. It's usually the first sign you've become someone they trust for the long game, not just the next invoice.

None of this works without the right delivery, though. A waiter who oversells the soufflé at every course ruins the meal. The line between helpful and pushy is trust, built one honest conversation at a time, not one pitch.

You can offer the soufflé without becoming the waiter who won't stop talking about it.

The goal was never to manufacture more work. It was to make sure a client who came in for appetizers didn't leave without knowing dessert was on the menu.

So what does it look like to fully step into being a high value strategic advisor? 

Start with building greater awareness of opportunities to go deeper with your curiosity.  Notice when the first answer isn't the whole answer. Don’t wait to be asked. Stay curious and unassuming enough to find out what the client actually needs, long after everyone in the room thinks the conversation is over.

Friends, this isn’t just to increase our revenue. This is to increase our value to our clients, serve them more deeply, and get better results with fewer headaches. 

Before your next kickoff, or your next check in with a current client, ask one question you're assuming you already know the answer to. See what it uncovers.