Read on: My website

Read time: 2 Minutes

You did not realize it was happening. A promise here. A contradiction there. A confused business development team. A lost client.

By the time you saw the damage, it was already done.

That board role you took to build credibility? It destroyed it instead.

Was this newsletter forwarded to you?

I remember the exact moment it became clear. A CEO I worked with was on stage at a state & local conference. He promised we would launch a new service upgrade by Q1. Nobody in that room knew what he was talking about. Not marketing. Not operations. Not business development. We found out at the same time the audience did.

We did not have a product. We did not have a plan. We had a CEO who said yes to a board seat and decided to wing it on stage.

We had to rewrite marketing collateral. We had to manage angry clients. We had to explain to our sales team why the CEO was making promises nobody could keep.

The financial hit was brutal. But the credibility hit was worse. Our team started to question whether leadership actually knew what it was doing. Our customers started to wonder if they could trust us.

That board role cost us $$$$ in lost deals, wasted resources, and damaged relationships. And it took months to rebuild what should never have been broken in the first place.

Here is the part that made me angry: He made that decision in a vacuum. He never asked his team. He never consulted his sales leadership, his operations team, or anyone else who would have to execute on what he said.

He just said yes and assumed we would catch up.

We could not. And it nearly cost us everything.

Let’s dance.


Want to get the most out of ChatGPT?

ChatGPT is a superpower if you know how to use it correctly.

Discover how HubSpot’s guide to AI can elevate both your productivity and creativity to get more things done.

Learn to automate tasks, enhance decision-making, and foster innovation with the power of AI.

Download the free guide


The Three Costs of Saying Yes Without Alignment

1. Team Confusion and Internal Chaos

When a CEO or a Senior Leadership joins a board and starts making public statements without internal vetting, your team does not know what is real.

Is this the new strategic direction? Are we pivoting? Do we need to replan the entire roadmap?

Your team spends energy trying to figure out what the CEO actually meant instead of focusing on execution. People get frustrated. Morale drops. The best people start looking elsewhere because they do not feel like they are part of the strategy.

A confused team is a stalled team.

2. External Credibility Collapse

Your customers are listening. Your competitors are listening. Your investors are listening.

If your CEO says one thing on a board and your sales team says something different to a prospect, that prospect notices the gap immediately.

Inconsistency kills trust faster than almost anything else. Your reputation in the market is built on consistency. When an executive contradicts the work your company is actually doing, you damage that reputation.

And once you lose credibility with a client, it is brutally hard to get it back.

3. Measurable Financial Damage

This is the cost nobody wants to calculate until it is too late.

Marketing collateral rewrites. Sales cycles that extend because of misalignment. Clients who churn because they feel misled. Time and money spent managing fallout instead of building the business.

I watched one board role cost a company half a million dollars. And that was just the direct costs. The opportunity cost, the deals that did not close, the partnerships that did not form, was double that.

The board role was supposed to open doors. Instead, it locked them.

Check out some of our other past issues here:

Hustling in the Human Lane 

When Chaos Hits, Accountability Wins 

Tech Breaks…Teams Don’t 


Red Flags: Know When to Say No

Before you even consider a board role, watch for these warning signs.

Red Flag 1: The board won’t give you clear answers on their lobbying priorities.

If you ask, “What policy initiatives are you actively supporting right now?” and the answer is vague, that is a problem. You need to know exactly what the board is pushing for and whether your company can publicly align with it.

If they are evasive, walk away.

Red Flag 2: Your leadership team immediately pushes back when you mention the board’s focus areas.

Your VP of Sales says, “Wait, they are pushing for that? We have clients who will be upset.” Your Head of Operations says, “We are not equipped to support that direction.” Your Government Affairs lead says, “That contradicts our current lobbying position.”

These are not minor concerns. These are warnings that internal alignment does not exist. Do not override them. Listen to them.

Red Flag 3: The board’s public statements already contradict your company’s existing client commitments.

Before you join, research what the board has said publicly. Then check if that aligns with your company’s actual client base and strategy.

If the board is actively lobbying for a bill that benefits one of your clients but harms another, you are walking into a minefield. You cannot serve both masters.

Red Flag 4: You feel pressured to say yes quickly without time to vet.

If the board is pushing you to commit fast, that is a signal. Good board roles allow for proper due diligence. If they are rushing you, ask why.

Usually, it means they know you would ask too many questions if you had time.


The Due Diligence Framework

If you are serious about a board role, do this work before you say yes. And do not do it alone.

Step 1: Get a Full Briefing From the Board

Schedule a formal meeting with board leadership. Your goal is to understand everything.

Ask these questions:

  • What are the board’s current strategic initiatives for the next 12 months?

  • What are the board’s top lobbying priorities right now? What policy initiatives are you actively supporting or opposing?

  • Who are the key stakeholders and what are the political dynamics?

  • What public commitments has the board made that I should know about?

  • If this is a state or regional council, what are the specific state-level or regional initiatives you are focusing on?

  • Are there any controversial positions or battles the board is part of?

Do not assume you already know. Get specifics.

Step 2: Run the Internal Alignment Meeting

This is the step most CEOs skip, and it is the one that costs them the most.

Before you commit, schedule a meeting with your leadership team. This is not optional. This is required.

Attendees: VP of Sales, Head of Marketing, Head of Operations, VP of Communications, Government Affairs lead (if you have one), and anyone else who will be affected by what you say or do on this board.

In this meeting, cover three things:

First: Lay out the facts.

“Here is what I am being asked to do. Here is what the board covers. Here are the topics and initiatives they are focused on. Here is the political landscape I will be stepping into.”

Let your team digest this information.

Second: Align on company position.

“The board is pushing for X policy initiative. Where do we stand on that? Are we for it? Against it? Neutral? Do we have clients who would be impacted by our public stance on this?”

Do not move forward until you have alignment on this.

Third: Vet the lobbying and policy initiatives.

This is critical. Ask your team directly:

“What lobbying efforts is this board focused on? Are we already lobbying on any of these issues? If so, are we aligned with the board’s position, or do we have opposing views?”

“Do any of our key clients or partners have opposing views on these policy issues? If I publicly support this board’s position, could it damage those relationships?”

“Are there any legislative battles or regulatory fights happening right now that we need to be careful about?”

Do not let this conversation stay abstract. Get specific. Get uncomfortable. Get the truth.

Fourth: Confirm your team can support what you might say.

“If I publicly commit to this board initiative, can we actually deliver on it? Does our product roadmap support it? Does our operations team have capacity? Does our sales team know how to sell it?”

If the answer is no to any of these, do not make the commitment.

Step 3: Establish Guard Rails

Make this clear before you say yes: I will not make any major public statements or commitments on behalf of this board without running them by this group first.

This is not about control. It is about alignment. It is about making sure you are representing the company accurately, not creating chaos.

Your team needs to know that you have their back, and you need to know that you have theirs.

Step 4: Keep Communication Alive

After board meetings, debrief with your leadership team. What was discussed? What is the board focusing on? How might it affect our business?

If the board is working on a lobbying effort that could impact your business, loop in your Government Affairs team immediately. Do not wait until it becomes a public issue.

Keep the conversation alive. Do not let information silos develop where you know what is happening on the board but your company does not.


The Decision Framework

Before you say yes to any board role, answer these three questions honestly:

Question 1: Can I publicly support this board’s initiatives without contradicting my company’s strategy?

If the board is pushing for something that conflicts with your company’s actual direction, the answer is no. Do not take the role.

Question 2: Does my team have the capacity and alignment to back up what I might say?

If your team is confused, conflicted, or unable to execute on board commitments, the answer is no. Do not take the role.

Question 3: Will this board role generate more value than it costs?

Will this build real credibility, open actual doors, create genuine relationships? Or is it just a resume builder that will drain your time and energy?

If you cannot answer yes to all three questions, the answer is no. Period. No matter how prestigious the ask feels. No matter how flattered you are.

A board role that costs you credibility and money is not an opportunity. It is a trap.


What the Internet Taught Me This Week

From new tools, recent trends, and market updates, here is what has been on my mind.

  1. Treasury cancels all Booz Allen contracts. Check it out here

  2. Small Business Administration Suspends 1,000 8(a) Firms for Not Submitting Data. Check it out here

  3. People Are Saying TikTok’s New Terms And Conditions Are Terrifying — Here’s What You Agreed To Share. Check it out here


Board seats are not vanity projects. They are strategic decisions that require rigorous internal vetting before you say yes.

The best board roles are the ones where your company is already aligned on the issues, where you can represent the company confidently because you have done the work, and where the role actually strengthens your business instead of weakening it.

The worst board roles are the ones where a CEO says yes in a vacuum, makes promises without consulting their team, and leaves the organization to clean up the mess.

Do not be that CEO.

Before you accept your next board role, run the internal alignment meeting. Get clarity on lobbying priorities. Confirm your team is aligned. Establish guard rails.

Do it this week. Before you make a commitment you cannot keep. Before you cost yourself half a million dollars and your credibility with it.

Your team deserves better. Your business deserves better. And so do your customers.

See you next week.


Whenever You’re Ready, Here are 4 Ways I Can Help You:

  1. Unlocking Hidden Potential – Reconnecting with Past Clients for Explosive Growth – Check out my free eBook on how you can find hidden gems in your past clients and help you crush your sales goals.

  2. AI for Business Development – Download our free eBook on how you can effectively leverage AI prompts to your advantage. From properly setting up your preferred AI tool, to how to shape your prompts, save time, and get the outputs you are looking for.

  3. Sales Resources at Your Fingertips – From tools, tips, demos, and how-tos, check out our Pages and content that can provide you with additional support, whether it be social selling, account management, or something else.

  4. Cribworks Advisor Program – Want more than just resources? Reach out to me and see if our Advisor Program can help you scale your business.