How to Lead with your Head, not your Heart

Don Rainey
Landing on your feet
4 min readJun 29, 2020

The startup CEO experience is an emotional one. Excitement, fear, desperation, exhilaration, exhaustion, all are certain to be part of your professional life at one point or another. Unlike other positions, however, the emotions you experience as CEO can have an enormous influence on others, and thus they can affect your organization immensely.

Photo by Tim Gouw on Unsplash

As a leader, your team will look to you daily for emotional clues. Your positive leadership gives them strength and optimism to overcome challenges. Yes, you may be discouraged or frustrated at times, but you must not let on. Superficially, it may feel not very ethical to “hide” these feelings from your co-workers. You want to be genuine and transparent, but a commitment to an honest and open environment has healthy limits.

There are times when you must consider the effect your exposure may have on your team. It is a bit like being a parent. You have to consider the best interests of your children as paramount. Ask yourself, is it in your staff’s best interests to see your genuine emotion at this time?

Sometimes the answer may be yes, but other times it may be no. Be aware of your presence and words when you are emotional. Understand that if you convey discouragement or frustration, it is contagious. The net effect of one person being discouraged versus everyone being discouraged is material. Will your demeanor inspire your team to try again?

Don’t discourage them further and make matters worse. If your discouragement is apparent but the source unknown, staff will usually incorrectly guess what it is and become depressed by another challenge.

I’ve had to deliver a fair amount of bad news to my employees, lost vital customers, small competitors becoming formidable from large financings, and layoffs. Leadership isn’t trying to paint bad news as positive. It is conveying positivity despite setbacks. Lead with your head, not your heart in tough times.

You must develop a plan to Work Wellfully when you are calm and rested so that when instances occur, you can limit the damage and move beyond these emotions to communicate professionally and in a manner that is in the best interests of your team. What specifically do you want to do to the team? Do you need to give information, or do you need to motivate them, or do you need them to be fearful of consequences?

It is impossible to control emotions and be purposeful unless you have a plan. (If you are already in a state, trying to decipher how to act will be useless. It is like telling someone to “calm down” when they are raging. It only makes things worse. )

Here are some steps to handling the inherent emotional challenge and building a plan to Work Wellfully.

Try to think first, feel second.

Remind yourself that nothing is as wrong as it initially appears. You will get some bad news. Hopefully, it won’t happen frequently, but it will occur. Your immediate reaction to bad news is essential. Before you sink in despair, consider the situation thoroughly. Think about the anticipated ramifications, of course, but also find what opportunities may be associated with it. Don’t assume the worst-case scenario. Try to think first, feel second. Prepare yourself to communicate with your team about the bad news. Anticipate their questions. Prepare to challenge them for possible opportunities that might coincide with the bad news.

Disengage and Refocus

Seek distance from the sources of frustration and chaos. Put them aside temporarily and work on other situations or problems. Recall the Pareto principle, that 20% of effort yields 80% of results, and re-prioritize your goals. Focus on things that are within your control. Lessen frustration by making progress on something that you can influence before you return to the current challenge.

Be conscious of expression

As a leader, be deliberate about expressing frustration or anger. There are many times it is desirable to express frustration with results or execution. It can sometimes be helpful for people to hear. You want to lead better results and improve operations. Speak calmly at all times — but especially when delivering bad or painful news. Don’t raise your voice. Statements are more powerful when delivered softly. Only express frustration and anger intentionally. When you have determined, it will be beneficial to communicate, choose your path for a desired effect.

Rest and Recharge

Problems loom larger when you’re exhausted. Don’t make any decisions final until rested. Everyone should have a plan for resting and recharging their emotional state. If you don’t take care of your physical self, you won’t be able to take care of your emotional self. Figure out what restores you and get at it.

Outsource recurring Sources frustration

Acknowledge recurring frustrations. Things that “get your goat” or people, systems, vendors that present continual issues need to be addressed. Re-valuate these tasks and relationships. Or re-define them. Outsource what you can. Seek help where you can. Eliminate them if you must. Do what you can to reduce scenarios that will trigger your frustration.

The startup experience takes an emotional toll. Develop a plan to keep to stay balanced and healthy while leading effectively. The importance of this goes well beyond individual mental health. It includes being aware of how to manage your emotions so that you only express them to your team when it is reasonable or helpful.

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Don Rainey
Landing on your feet

Veteran venture capitalist and father of six. Love life and the startup experience. I write to pass along what I’ve learned.