Why Sales Leadership is so HARD and How to Minimize the Stress

When you get promoted in sales it’s typically because you were a top performer. You had grit, drive, work ethic and a good attitude but there is a good chance you didn’t have a lot of leadership experience. Or maybe you did, but you didn't have a lot of sales leadership experience.

Either way, you walk into a whole new world and suddenly reality slaps you in the face. You have the stark realization that you no longer have control over your performance. Now, your performance relies on a team of people who most likely do not work the way you did and probably aren’t self sufficient. They may not be able to take feedback and could have a million personal issues that you now have to deal with.

Suddenly the vast majority of your time is spent trying to teach other people how to do their jobs, convincing them to actually do it while simultaneously keeping them happy.

Your direct reports will want all of your emotion, motivation and culture building. Meanwhile everyone above you wants data, performance, logic and plans. You have to strike a balance between the two that can be exhausting.

Hopefully you will get a couple top performers on your team but you might soon discover that often your top performers are the highest maintenance. They need you to cheer them on, motivate them and give them recognition. You also have to fight for your team around ROE, leads and promotions, and at the same time hitting all the goals that you have set. All while trying to not forget about yourself.

Let me be VERY CLEAR here that sales leadership is also invigorating, inspiring and very rewarding. It is my dream job and I am fortunate to get to live it everyday. This article isn’t about the all the best things, it’s about dealing with the tough side.

Sales is exhausting and sales leadership can be depleting. But there are ways to make your job easier, so that you will be able to do your dream job and get all of the positive of sales leadership with far less of the tough side.

  1. Delegate and create independent salespeople - The worst thing you can do to your people, is doing everything for them. If you create a dependency from your salespeople it will make your job ten times harder. Instead teach your people how to be independent by always challenging them to come to you with solutions instead of problems. Ask them “What do you think you should do?” when they ask questions that they should know or could easily find the answer to. Learn how to delegate! The rule is: DO NOT do anything for your team that they can do for themselves. Example: Instead of you telling them what their commit and plan is, make them come with their commit and plan. Instead of you sending the email recap after your one on one, make them send it. It not only saves you time but also give you a clearer picture of what they derived from the conversation.

  2. Realize not everyone is you - You were a hard worker, a great salesperson and you had a specific way of doing things. It is highly unlikely that you will ever have a YOU on your team. That does not mean you cannot hold your team to high standards, just understand people may go about their approach and technique in a different way. It is your job as a leader to figure out what works for each of your people and help use their strengths. It is not to create a bunch of YOU’s. The sooner you realize this the less stress you will have.

  3. Your sales reps are not your friends - I love my people. I will do anything for my teams. However, they are not my friends. It is great to be liked but NEEDing to be liked is the worst characteristic a leader can have. The leader that needs to be liked will never do what their team needs them to do, they will do what their team WANTS them to do. As a leader you have to make tough choices, you have to raise the bar and you have to push people to be their best. If you are worried about them liking you, you will never get them to where they need to be. By letting the need to be liked go, the tough conversations and choices won’t be as stressful.

  4. DOCUMENT EVERYTHING - It is horrible when you have someone who has been underperforming or has a bad attitude and you get to the point where you are ready to let them go but you haven’t documented anything to this point. Or you let someone go and they act surprised and tell HR “I had no idea I had this issue, my manager never told me.” If this happens, you did not do your job as a leader. Have the conversations early and often and get in the habit of having your people send you an email recap after every single one on one. Document all of your one on ones with your boss as well. Having written documentation will help you continue to grow your people, yourself and it brings clarity to all parties. It reduces stress because expectations are clear and everyone knows where they stand.

  5. Practice ACCOUNTABILITY - Set standards and expectations for your team and hold them accountable to those expectations daily. Call out all the slips and make sure you follow through with any conversation you have. This is NOT micro-managing, this is about accountability to set expectations. It is when we let things slide because we think they will fix themselves that it becomes a snowball effect. Accountability for yourself and your team is the best thing you can do everyday to eliminate stress because it will help you stay ahead of any issue before it becomes irreparable.

  6. Have fun and don’t take everything so seriously - Relax! The team takes the tone of the leader and if you wear your stress on the sales floor, your team will be feeling and it will show in their performance. Salespeople perform when they are happy, confident and supported. If you bring your stress to your team you will definitely see the effects. Besides, stressing will not get you any closer to quota.

Sales leaders are a special breed. We handle emotions, pressure, motivation and still bring in millions of dollars for our companies. I couldn’t be more proud of what I do and you should be too because we make people better every single day. At first it isn’t easy, but you can make it much easier by doing these things everyday to reduce the stresses that come with the job. Eventually when you master these skills, everyday is the best day and you get to focus on the fun things like HITTING QUOTA!