Dear Crucial Skills,

I’m a cofounder of a company that recently brought in a new CEO who I don’t know well. I want to talk to the CEO about taking an executive role in the company and obtaining his mentorship. The problem is I feel very strongly about this position and my contribution, and tend to get emotional about it. I know I’ve made a very significant contribution to the company’s growth, but I’m also fundamentally insecure about my skills. I also don’t have the resume that investors are looking for. The new CEO is a very level-headed person who doesn’t get emotional about anything, and I don’t want to lose credibility with him as I negotiate my role in this growing company. Can you give me some pointers for preparing for this conversation?

Sincerely,
Looking for a Promotion

Dear Looking,

Of course you get emotional about your role in the company you cofounded! This company is your brainchild; you’ve invested your blood, sweat, and tears. Any conversation about your role going forward is high stakes indeed. And strong emotions are often the biggest barrier to effectively influencing others. As you take stock of the company’s needs, and of the skills you need in order to fulfill an executive role, you are wise to seek the new CEO’s mentorship. So how do you have the crucial conversation with the CEO about taking on an executive role?

Start with heart. As you contemplate having this conversation, ask yourself, “What do I really want? For myself? For the new CEO? For the company?” Of course you want the company to be successful. You also want to support the CEO and help him succeed. In addition, you want to occupy an executive position and be effective in that role. Keep in mind that you are not a beggar or a thief. You are not asking for a position you do not deserve, nor are you expecting a role that benefits you and hurts the company. You want to add value and make a meaningful contribution. These are good motives—helpful motives. As you focus on these thoughts, your brain will be in gear and your emotions will dissipate.

Create mutual purpose. An important beginning to this crucial conversation is to help the CEO understand your intentions—your motives. You might want to say something like, “I want to talk with you about my role in the company. I am absolutely committed to making the company succeed. I also want to do everything within my power to help you be successful in your new role as CEO.” Such a strong declaration will do a lot to make it safe for the CEO to discuss the topic with you openly.

Next, share your meaning. As with bringing up any sensitive topic, I would encourage you to share the facts. Help the CEO understand your history with the company and the many contributions you’ve made. There’s no need to feel embarrassed or shy. You are not bragging or “tooting your own horn.” You are giving the CEO important information he needs to make decisions about how to best utilize your abilities. Then tell your story by sharing with the CEO your honest evaluation of your strengths and weaknesses. Our tendency is to ‘spin’ our histories by embellishing our strengths and understating our weaknesses.

I once worked with a colleague who was always trying to ‘sell’ me. When advocating his point of view, he emphasized the reasons to do what he wanted, and left unmentioned the downside. I grew to discount his statements and distrust his motives. You do not want to do this. Identify where you see yourself as the most capable and where you need more development. This kind of honesty, openness, and insight will help your CEO appreciate the kind of person you are and trust your candor. Next, make your proposal. Explain the position you want to fill and its responsibilities. Ask that the CEO mentor you and help you strengthen the areas you’ve identified for improvement.

Finally, ask for the CEO’s input. You’ve put a lot of meaning in the pool; now is the time to get his. Ask questions and listen. How does he see the situation? How does he view the fit between you and the executive position?

This appeal will not necessarily guarantee that you end up with the position you desire. However, this approach will increase the likelihood your emotions will not get in the way, and there will be greater mutual understanding.

Good Luck,
Ron