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red flags and green flags before working with someone

Green Flags (and Red Flags): How to Spot a Great Partner Before You Sign Anything

Mar 8, 2026/in Advice, Blogging, Marketing/by Jeph Maystruck

Green Flags: How to Spot a Great Partner Before You Sign Anything

We talk a lot about red flags.
But green flags? Those are harder to name, and way more useful.

A great partner doesn’t scream their value.
They signal it.

Here’s what to watch for.

🟢 They Ask Better Questions Than You Do

A green-flag partner doesn’t rush to solutions.

They slow the room down.

They ask things like:

  • “What’s the real problem we’re solving?”
  • “What happens if we don’t do this?”
  • “Who is this actually for?”

If someone jumps straight to tactics without understanding context, they’re guessing.
And guessing gets expensive. We don’t like guessing.

🟢 They’re Comfortable Saying “No” (or “Not Yet”)

This one’s huge.

Great partners don’t say yes to everything, even when money is on the table. SPECIALLY when money is on the table. You can tell a startup from an experienced company. The startup says “yes,” they can do everything! The experienced company only does one or a few things REALLY well. Be careful with those who say they can do it all. Think Jim Collins and his hedgehog concept.

They’ll say:

  • “That’s outside our wheelhouse.”
  • “We could do that, but I don’t think we should.”
  • “There’s a better way, want to hear it?”

If someone never pushes back, they’re not partnering.
They’re complying.

🟢 They Explain the Why, Not Just the What

You’re not just buying output.
You’re buying judgment. Strategy. Purpose. Things are done with intention, not “just because we’ve always done it!”

Green-flag partners walk you through their thinking:

  • Why this approach
  • Why now
  • Why not the other thing you suggested

They want you to understand, not just approve with a rubber stamp.

That’s confidence, not arrogance.

🟢 They Respect Your Time (Before They Ever Bill You)

Watch how they behave before the contract.

Do they:

  • Show up prepared?
  • Follow up when they say they will?
  • Keep meetings focused and purposeful?

If they waste your time before you’re paying them, they’ll waste more after.

Time respect is culture revealed.

🟢 They Don’t Try to Sound Smart, They Try to Be Clear

Big words don’t equal big brains. After all, it’s easy to make a simple concept confusing; it takes a real genius to make a difficult concept sound easy. The idea of “explain this to me as if I were a 5-year-old” is a good start!

Green-flag partners:

  • Use plain language
  • Avoid unnecessary jargon
  • Can explain complex ideas simply

If someone hides behind buzzwords, they’re either insecure or selling smoke.

Clarity is generosity. Simplicity is genius.

🟢 They Care About Outcomes, Not Just Deliverables

A great partner isn’t obsessed with checking boxes. It’s not about getting through your checklist, it’s about doing something that matters that you can measure.

They care about:

  • What success actually looks like
  • How this connects to your bigger goals
  • Whether the work actually worked
  • If mistakes were made they admit it

They’ll ask:

  • “How will we know this was successful?”
  • “What does ‘good’ look like six months from now?”
  • They always begin with the end in mind

That’s someone thinking long-term, with you.

🟢 They’re Curious About You, Not Just Your Budget

If the conversation feels transactional, that’s a warning. If all they want to do is to get you to sign on the bottom line they’re not going to be a great partner. You know the sales people, they treat you like gold before you sign, once the contract is in place you never hear from them again. It’s a tale as old as time. Be wary of the contract pushers! That’s all they’re good at.

Green flags show up as genuine curiosity:

  • Your constraints
  • Your pressures
  • Your internal politics
  • Your values

They want to understand the humans involved, because that’s where projects live or die.

🟢 They Don’t Pretend to Be the Hero

This is a big one.

Great partners don’t position themselves as the saviour. They position themselves as the guide. As the facilitator, the teacher. Not the heroic partner that will solve all your problems.

They don’t say:

  • “We’ll fix everything.”
    They say:
  • “We’ll figure this out together.”

Ego-heavy partners create dependency. Healthy partners build capability.

🟢 They’re Optimistic, Not Delusional

You want belief, not fantasy. Sure, ideation sessions can get out of hand, but a real partner will bring you back down to reality to understand what we can actually deliver, not just brainstorm incredible ideas. Because remember, ideas are a dime a dozen these days, anyone can come up with a great idea! The real genius comes with execution. Launching something. Shipping something. Putting something out there that you can get feedback on.

Green-flag partners:

  • Acknowledge risks
  • Talk openly about trade-offs
  • Set realistic expectations
  • Always give you other options

They’re hopeful and honest. A great partner will tell you if they don’t think something will work.

That combo is rare. When you find it, pay attention.

🟢 You Feel Calmer After Talking to Them

This might be the most important one. You can get a hold of them easily, and after a conversation, you’re put at ease. Highly underrated in many industries, just being available.

After the call, ask yourself:

  • Do I feel clearer?
  • Do I feel less alone in the problem?
  • Do I feel like someone has my back?

If the answer is yes, that’s not accidental.

That’s trust starting to form.

The Gut Check

Before you sign anything, ask yourself one final question:

“Would I want this person in the room when things go sideways?”

Because they will.
Things always do.

If the answer is yes, green flag.
If the answer is “ehhh…”, listen to that.

Okay, what you’ve all been waiting for….THE RED FLAGS!!

Red flags working with people in an office

The Dreaded Red Flags

🚩 “We just need this to go viral.”

Ah yes. The most sophisticated marketing strategy known to mankind.
Right up there with “Let’s just win the lottery.”

Going “viral” is an outcome, not a strategy. Run, don’t walk away from these folks!

🚩  They want a proposal before a conversation.

Before we talk about goals.
Before we talk customers.
Before we talk reality.
Sure. Let me just consult my crystal ball. If all they want is a proposal, they are price shopping. The same way you’d buy a used car. But that’s not what you’re selling. Remember, someone is always willing to go broke before you, so stop trying to compete on price. Folks who just want the cheapest ______ will surely leave you for someone else that’s offering what you do for cheaper.

Sorry, we don’t negotiate with price terrorists. (an actual policy at StratLab! HA!)

🚩 Everything is urgent.

If every project is a five-alarm fire, you don’t have a marketing problem.
You have a planning problem.

You know what stresses a team out? Last minute requests. If you can’t give a project the ample time it needs, what are the odds it’s going to be awesome anyway? If someone is always in a rush, you’ve just signed up for heightened stress levels. Don’t do it. Remember what Alabama said? I’m in a hurry and don’t know why. 

🚩 “We tried (ANY idea) once. It didn’t work.”

Amazing. Tell me more about the boosted Facebook post your nephew ran in 2018. Congrats for remembering!

We’ve all been in those meetings with idea assassins? Whatever you come up with, they’ll tell you why it won’t work, or didn’t work

🚩 They negotiate price, not scope.

Healthy clients ask:
“What could we accomplish at different investment levels?”

Red flag clients ask:
“Can you do the same thing… but for half?” 

Remember, don’t negotiate with price terrorists! Anyone who isn’t willing to spend money on what you’re selling isn’t going to be a great customer anyway! And the last thing you want are bad customers! They’re worse than no customers!

🚩 They want to approve every tiny detail.

Every headline.
Every colour.
Every comma.

If you’re hiring experts but don’t trust them, congratulations, you’ve just invented the world’s slowest project.

Work with people who trust you. Approvals are fine, but not for every little detail.

🚩 No clear decision maker.

Five people in the meeting. Seven opinions.
A Google Doc full of comments. And somehow… nobody actually decides anything. (insert eye-roll)

People who don’t want to take accountability are the same ones who are worried about what others will say. Leadership means the buck stops with you. If you want to be a leader, you will take the blame when things go wrong. But that’s a good thing, holding yourself accountable is rare in business these days, if you do it, you will stand out like a sore yet likable thumb!

The best leaders know they won’t be wrong or right about everything. Being wrong humbles you; it also shows you’re willing to have a bad idea, which is also very rare in business. Being wrong makes you more human. Being a human is a good thing.

🚩 They obsess over competitors.

“What are they doing?”

I don’t know.
But I promise they’re not sitting around worrying about you this much. Early in business, we’d encourage the competition, we’d bash the companies they were going against, but that was merely playground tactics. In business, good business, folks don’t bash their competitors; they learn from them.

If all you’re doing it worrying about your compeitiors then you aren’t doing what you should be doing.

🚩 Marketing is treated like a cost to minimize.

If the whole strategy is “spend as little as possible,” the outcome will usually match. Marketing should be building something, creating something, and that something should be measured. Many folks treat marketing as a necessary evil, a short-term expense with no long-term benefit.

I like the old adage, you get exactly out of your marketing strategy what you put into it. Treat it like a cost centre that doesn’t deserve your attention, and I guarantee you won’t be happy with your marketing. Treat it like an investment that will be repaid over and over again in time, then you’re going to approach it differently.

Be careful when you’re a cost centre to a business, as your long-term strategy is becoming obsolete. Instead, you’re a profit centre just waiting to happen. Measure your marketing spend, determine your return on it. It’s an investment, but if you don’t track it, it will become a cost centre.

Red flags vs green flags

 

Tags: being human, business strategy, Clients, communication strategy, leadership, psychology
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https://strategylab.ca/wp-content/uploads/2026/02/red-flags-and-green-flags-before-working-with-someone.jpg 1024 1536 Jeph Maystruck /wp-content/uploads/2023/11/SL-2023-Logo-White-1030x363.png Jeph Maystruck2026-03-08 09:17:452026-03-09 14:58:13Green Flags (and Red Flags): How to Spot a Great Partner Before You Sign Anything
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