Sales Coaching is Hard

I get it… sales coaching is one of the hardest things you do as a sales leader. Managing people is never easy.

Once you get into management, there is no more cold calling, chasing contracts, or constant asks from your manager about deals in the pipeline. Life as someone “carrying a bag” (quota-carrying) is a life that experiences more failure than success. So is sales coaching really what it’s typed up to be?

In fact, in B2B SaaS sales development reps fail 80-90% of the time. After having interviewed close to 200 candidates to join my teams in the past as a sales leader, their typical career progression goals always seemed to involve getting into some level of sales leadership. 

Once, just once, I want a candidate to be honest and tell me that they are done chasing contracts and cold calling. Instead, I’m told “I want to make an impact”, or “I want to lead a team” type answers. This is where I immediately lose interest in the candidate.

Truth be told… sales leadership isn’t for everyone because most don’t even understand where to start with sales coaching. Let me tell you why. 

Leadership & Coaching Go Hand In Hand

1. Sales Managers work longer hours – When the sales team and everyone else from the office leave the office to go home, you are left updating your CEO on deals, chasing internal product updates, or reviewing calls. “Normal business hours” are for sales calls and supporting your team, and administrative hours are for weekends and after dinner. Most sales development reps don’t understand that.
2. Sales Managers make less money – Typically, as a sales leader, your compensation structure is more like a bonus. You earn a chunk of money at the end of a quarter if your team hits certain revenue goals. Whereas sales development reps get incentivized monthly or even weekly. The accelerators that reward for performance above and beyond quota are not that enticing, and sometimes if you don’t hit a certain percentage of the goal then you might not make anything at all. 
3. Your job is to absorb the downstream stress – As a Sales Leader, you are supposed to act like body armor, potentially shielding your team from the board, the CEO… anyone up top who is putting pressure on the sales team. A good Sales Leader takes 80% themselves, and then gently passes along the rest to the team. This is where good sales coaching comes to play.
4. Gone are the days of ringing the “gong” – The newbie closes their first deal, although you did 90% of the work. They hit the gong, they get recognition. You are no longer the center of attention when wins come in. Welcome to being a leader.
5. When your Sales Team fails, it’s the Sales Manager’s fault. When the Sales Team wins, the Sales Team did it – Accepting personal responsibility for the failure to hit your number, and not blaming the product, marketing, or your team is difficult. The only person to blame is yourself when you miss your number. This is why sales coaching and sales leadership are synonymous. 
6. No excuses – The product fails to deliver, marketing does not generate enough leads, customer success doesn’t support the customers well enough to generate references… none of this matters. Everyone else in the company could fail, but Sales Managers are still expected to perform. You literally are responsible for the company’s sales revenue, regardless of any “excuses”.
7. Start at $0 4 times a year – Want to get kicked in the teeth 4 times a year? Try crushing your number in Q1 and then waking up in Q2 to the realization that NOTHING you did as Sales Manager yesterday matters. You and your Sales Team will be solely judged on your performance for the next 90 days. 
8. Sales Coaching – I remember when my dad used to teach me how to dribble a soccer ball with my left foot. We would practice every day for hours after school, and then when the game came and I was faced with a defender in front of me I would freeze and revert back to my right foot. Sales coaching is a little like that. You can invest hours and hours in role-playing, however, the moment the pressure comes up, that is when the coaching needs to happen. 

So why would anyone EVER want to get into Sales Management? 

You have tremendous stress, make less money, work longer hours, and are only as good as your last quarter. 

Let me tell you why I do it. 

1. Capability to make a tremendous impact on someone’s future – Being able to watch as a new sales development rep goes from “scraping” trying to close their first deal to buying their first nice car, buying a house, gaining the confidence to ask someone out on a date. Knowing that the time invested in that person actually is improving their life for now and forever. I can tell you the name of every sales representative I have ever managed, and what impact their role on my Sales Team had on their life. 
2. Career progression – This ties into the first point, but I do believe it is separate. Being able to say to myself “I helped this person get to a better place today than they were when they walked in here”. If someone on my team hasn’t learned new skills or progressed their career to the point where they are being recruited away from me, then I haven’t done my job. I have failed as a Sales Leader. 
3. Embraced unselfishness – I can still remember the first time I closed the majority of a deal for a rep on my team, and I watched as they hit the gong, they got the high fives and I encouraged all of the recognition for the rep without taking any for myself. This skill has helped me so much in my own life; it has allowed me to bolster people around me and shifted the reward to my internal feeling of recognition when someone else wins with my help from behind the scenes. 
4. The stress – On December 31st at 11:30pm when a rep and I are pulling out all the stops together to win a deal, and then it comes through at 11:58pm… damn, it feels good! Fighting to win alongside someone, and helping them succeed when the pressure is on is a great feeling! 
5. Taught me to be a good dad – Nothing teaches you perseverance, patience, humility, and 100 other good traits like being the person who takes all the punishment and gets a little reward. Watching my little man grow up, I can say without a doubt that the skills I have learned helping fresh college grads earn the chance at being in the top 1% of all income earners by the time they are 23 will beyond doubt help me mentor my son to success. Hard work and never giving up. 

Yes, the money is good (but not as good as a top sales development rep), but I will undoubtedly say that the real reward for getting into sales leadership is the personality and character developed throughout the process.

Don’t think sales coaching and sales leadership are similar? Tell us why.