You’re Never Too Awesome to Have a Coach

a single sprout emerging from the dirt

Sales coaching has many different forms. On bigger teams, it can come from sales leaders in player/coach roles, sales operations leaders, and more. There are also many Slack micro-communities where reps help each other learn. I’ve only worked for startups where sales coaches aren’t always made readily available and right now, I work with two sales coaches. While there are many ways to learn, the formality of having official coaching really resonates with my learning style.

When looking for a coach, it’s important to keep your specific goals in mind. Between my two coaches, Matt Wanty specializes in cold outreach and has helped me put messaging in place at two startups so far. Meanwhile, Matt Wolach works with SaaS startup founders like myself to help them scale their sales organizations (yes, you do need to be named Matt to coach me – just kidding). Your coach(es) expertise needs to align with your individual goals in order for you to gain the most from the relationship.

Coaching accelerates professional development. For example, in sales we use many different channels to reach prospects and influence buying decisions. It’s difficult to know if you are reading the room correctly while you are in the middle of your pitch. A coach helps you make sense of what you did so that you do it better, or sometimes differently next time.

Here’s how coaching helped me ramp faster in my first SaaS sales role:

  • Having an outbound sales expert review my messaging helped me improve it quickly.
  • Explaining my product and industry to someone else forced me to simplify my pitch.
  • Dedicating time for coaching kept me accountable for my progress.

According to Carol Dweck (author of Mindset), “People with a fixed mindset—those who believe that abilities are fixed—are less likely to flourish than those with a growth mindset—those who believe that abilities can be developed.” Making time for coaching and actively improving keeps me in a growth mindset. If you’re like me and naturally tend to have a fixed mindset, this is critical. 

While the benefits are apparent, there are a few myths about coaching that keep reps from seeking help.

Myth #1: If a rep hires a coach, their manager must be terrible.

  • This one is just silly. Managers can be great coaches, but that doesn’t make a rep wrong for dedicating more resources to their development. There is value in having input from outside your organization, in addition to what your manager offers. That doesn’t make your manager bad.
  • In startup roles like mine, managers are incredibly busy and often appreciate the initiative of reps who improve independently. 

Myth #2: Having a coach means you are bad at your job. Why else would you hire a coach?

  • Every amazing athlete has a coach. Plenty of top executives have coaches. In sales, why do we feel like there should be a point when we “graduate” from being coached to coaching? This kind of attitude is wrapped up in ego – not uncommon in sales – and can be detrimental to the growth of both you and your team. 
  • Having a coach does not exclude you from being a coach yourself. When reps reach out to me for help, I try to make time for at least one call to help them. It’s always rewarding when I get feedback that my ideas were helpful. 

Myth #3: It’s too hard to know which coaches are good. 

  • It’s true that there are a lot of coaches and many of them are out of touch because they haven’t sold in a long time or have forgotten what it’s like to sell to ICPs other than sales leaders.
    • Years ago, I had a bad experience with a coach. He led a training for my team and I thought his tactics lacked integrity and common sense. He turned me off of coaching for a while. Being burned feels bad but one bad coach doesn’t mean all coaches are bad. Don’t let one bad coach keep you from getting good expertise later on.
  • To narrow down which coach is right for you, consider these factors:
    • What industries and personas are you targeting? Ask coaches what their experience is with them. Don’t accept “sales is the same everywhere” as an answer.
    • What are your top goals? Ask coaches how they would coach to those specific goals. For me as a startup cofounder, I’m working on getting our first sales in the door and building the brand. For someone else, it might be moving up the career ladder or improving close rates.

Myth #4: If I can’t afford coaching, I’m out of luck.

  • There are many ways to get the experience of being coached for free. 
  • Make time to listen to your own calls (a form of self-coaching). Take the time to really hear the questions and answers after the pressure of the moment has passed. If possible, have someone else listen to your calls as well. Their insight is even more valuable because they come with a fresh perspective and no baggage.
  • Join a Slack sales micro-community and start asking questions, even if you feel vulnerable about what you ask. 
  • Ask other reps to practice cold calling with you, especially reps from other companies who don’t know your product well.

Sales technology, best practices, and channels change over time. Committing to coaching is part of keeping skills sharp in a fast-paced world. For me as a first-time founder at, coaching is part of how I make every day count. 

To learn more about, and see how they use a data-driven approach to pick the best candidates for sales roles, give Anjali a ping over on LinkedIn.