How to Balance Closing Deals with Coaching Reps as a Sales Leader

As a sales leader, you know how to impact the biggest deals… but how do you balance being the “hero closer” while helping your team up-level their game?

When you have big revenue targets to hit, especially at an early stage company, it’s easy to want to jump into every deal – but it’s also important to keep the long game in mind. Your role as a sales leader should be focused more on empowering your reps to win, and less on winning deals yourself.

What’s the best way to help your reps close deals without overstepping? We talked to three B2B sales leaders about this balance in a masterclass – get their advice below!

Meet the experts: 

  • Nasri EL-Sayegh, VP of Sales at Hokodo – sales process & methodology geek and scale-up leader
  • Olivier L’Abbe, SaaS GTM Operator & Advisor – 20+ year GTM leader, former president at Metadata & senior sales leader at G2 
  • Stratton Glaittli, Director of Sales at TOOLBX – previous Wayfair B2B Senior Sales Manager creating & growing the Utah location to 120+ reps

1. Complement and coach your reps on deals – don’t steamroll them 🚂

If you’re a sales leader, chances are you were an A+ rep. It can be hard to break out of IC mode when making the shift to leadership, especially when you know you can impact key deals and drive revenue.

Shifting your mindset and setting boundaries for your role as a sales leader is crucial. You can (and should) still help close deals, but prioritize partnering and coaching first.

“Ideally, I want my reps to be able to do everything I can do. I’m always thinking about how I can make something a coachable moment.” -Stratton Glaittli

If you’re joining a prospect or customer call, make sure you’re complementing them and not steamrolling them – you’re a team. Model best practices so they can observe and try them out on their next call.

Bonus tip: Make sure you understand your reps’ career goals and where they are on the path to achieving them. As a leader, part of your role is helping them get to the next level.

2. Over-prepare for prospect/customer calls and assign each person a role 🙋

One way to help your reps close deals without overstepping is to help them relentlessly prepare for each important call.

“Every good leader should hold a pre-meeting prep call. ‘These are the questions we want to ask, the objections we think we’ll get and how we’re going to handle them’ – so you have a game plan going into it.” -Nasri El-Sayegh

You should also assign a specific role to everyone on the call, including yourself. Figure out what value each person brings, which questions or points they should bring up, etc. so your team is a united front, instead of talking over each other.

Help your reps to think strategically about inviting other stakeholders. Nasri’s team at Hokodo knows that whenever they invite him to join a call, he’s going to ask what they want him to do – what’s the value he can add to the conversation?

After the call, do a quick recap with your reps – ask what they think went well, what they learned, and if they have any questions. It helps ensure they’re picking up on behaviors and best practices.

Bonus tip: Record every sales call and do a weekly listening & review session with your entire team. Highlight one rep’s call and walk through what they did and what others can learn from it. 

3. Leverage executive sponsors effectively 👑

Executive sponsors, whether it’s you as the sales leader or your founder, CEO, etc., can be a great way to move the needle on key deals – but make sure your team knows how (and when) to leverage them effectively.

At the beginning of every quarter, identify your highest-priority deals – which ones will move the needle from either a revenue or a logo/brand recognition perspective – and break down the skills required to close them. (For example, some deals might need more technical knowledge from your team, or more financial expertise.)

Assign an executive sponsor to each key deal based on their skills. Then they can reach out to the champion or other stakeholders to introduce themselves and offer their help. This also saves the sales leaders from being the executive sponsor every time!

Because we’re in a downturn, it’s also taking longer and involving more people to make a decision – so make sure you’re helping your reps identify ways to speed up the process. Coach them on not being afraid to ask their buyers tough questions.

“If I’m a leader who’s asked to join a call, I want us to request something in return,” Olivier said. “Like, ‘I need your VP on the call too so we can fast-track this decision process.’”

Bonus tip: Invest in enablement earlier than you think you need to. There are so many options for great sales tech which can help you get insights into how your team is operating and where to improve.

“If you can invest in enablement, your sales leaders won't have to help close a lot of deals at the end of the quarter. More importantly, you’ll empower your team by enabling them to be successful." -Olivier L'Abbe

Watch the full masterclass: