CIO Leadership

Two Reasons You Fail To Persuade Other Leaders And How To Change It

We hear a lot about tactics when it comes to persuasion. Relatability and confidence are more effective; unfortunately, what they mean is often misunderstood.

Joe Woodruff


January 26, 2023

How do you get leaders to do what you want without having to master principles and the art of persuasion?

“You don’t want to be heard; you want to silence.”

I have never been swayed by the masses, but I have been persuaded by one person’s thinking.

Leaders lead leaders. You rise above your rank as you serve well, solicit feedback and set priorities. But it’s not enough. At some point, you have to sell; you have to persuade. You have to lead to an outcome that you want.

As one person recently told me, “Politics is the art of letting other people get your way.”

But here’s the deal: You can master all the principles of persuasion - such as scarcity, social proof, authority, reciprocity - and still fall short. 

And the reason you fall short is because persuasion isn’t first about principles or strategies. It’s about two great human needs: a solution and a solver (history and news are filled with this theme - sin and a savior, hell and a hero, challenge and a conqueror). 

None of us are exempt. There is always something in front of us that needs an answer; there is always something within us that looks for a person or group with the answer. 

When we lose sight of this, we fail to persuade other leaders because of (1) how we relate to them and (2) the way in which we relate to them.


Persuasion is anchored in being relatable. But we misunderstand relatability to mean likability. Being likable is great, but I like a lot of people who don’t persuade me, and there are some people I don’t care for who do persuade me.

What is happening?

Relatability is based on need, not likability. If you understand my need, I believe that you get me. And if you share a need that I can relate to, I feel as if I get you.

This is why most “sales” conversations and presentations miss the mark: We try to be likable instead of relatable, so we find common interests, employ humor, tell stories that don’t seem to, well, relate to the matter at hand. 

Instead, relatability is communicated in four strong approaches.

  1. I clearly communicate the need that you are facing and the tension in it. I understand it.
  2. I share my experience of the need. I have lived it too.
  3. I shift to “we” language in the solution.
  4. I make a direct appeal as to what must be done next.


(1) “Leadership transitions can be tricky. People wonder what changes will be coming, how they will fit with those changes, if their work load is going to be more or if they will even have work. 

(2) I remember one major transition I suffered through: A new young leader with an aggressive change philosophy came in pretending to collaborate while really imposing his own agenda. I didn’t last a year. How do you transition leaders confidently so that you strengthen morale and build hope? 

(3) I found three essentials. We need to rally the right people, craft strategy together and drive change with over-communication. 

(4) If we don’t commit to this, we will continue to handle unnecessary concerns that distract from our mission. But if we do this, we will see morale increase, engagement strengthen and willingness to work extra. We have one clear first step. We have to invest in a communication portal that is devoted to news, updates and celebration about the transition.”

State the need. Connect to the need. Speak to the need. Resolve the need. That is how you are relatable.


Relatability around need is how we relate. Confidence is the way in which we relate

You cannot persuade someone to have confidence in you; but your confidence can be persuasive.

Confidence is not the property of any one personality type. It’s not the sum of formulaic parts.

Confidence is a bearing before it ever gets a hearing. And you are confident if the following is true:

  1. You are aware of a need.
  2. You know you have a solution to the need.
  3. You know a person’s or group’s motivation and what they value in a solution.
  4. You are genuine in seeing and seeking what is best for them.
  5. You know that you are not even remotely defined or diminished by their decision to embrace your solution or not.

Confidence is the property of the one who serves. Confidence is your leverage to rise above your rank.

When you look at the five bases of confidence, everything flows to and flows from point 3: knowing motivation and value. 

Leaders want to alleviate a pain or acquire a gain. At some point, a trigger occurs that makes a person more open to your solution.

How do you find another leader’s motivation?

  • Ask. What one thing, if anything, do you need to avoid most in (X)? What is the best outcome you are seeking for (X)?
  • Think. From what you know, what would be hell for this leader? What would be heaven? How does your solution (what you want for them) save them from one and get them to the other?
  • Spy. People gossip. What are you picking up on that can help you dial in on current motivation and the value (time, energy, ability, money) someone is willing to invest towards a solution.

James K. A. Smith wrote, “To be human is to be on the move, pursuing something, after something. We are like existential sharks: we have to move to live.”

To persuade leaders, you need to move with them, not just call to them. They are hounded by voices. You don’t want to be heard; first, you want to silence. Then you will be heard.

Capturing their attention by relating to their need, and being a confident presence in answer to their search, transforms your influence and meets their ideal.

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