Doing good coaching is difficult. But its impact is undeniable, particularly in sales teams, where so much is on the line. It starts with radical candor, showing empathy, and being willing to support directly. Be aware, AI might soon change the coaching game.

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Radical Candor

I am, was, and will always be a team player. I'm a firm believer that the best functioning teams - the ones who consistently achieve better outcomes - are able to put their heads together and collaborate constructively 💪

A leader is responsible for building and maintaining a strong, positive culture of collaboration. It starts with coaching.

The Radical Candor framework has always been the North Star approach to coaching. Imagine two axes: The ability to care personally and the ability to challenge directly. Leaders displaying radical candor with their team members care enough about the person to challenge them directly.

The importance of coaching in sales

In B2B sales, coaching plays an important role. Pushing deals through the sales funnel can be ambiguous and nuanced for individual salespeople. As a result, they need tactical support from more experienced colleagues (read: "their manager") to learn best practices, tips, and tricks to navigate the sales cycle.

The impact of effective coaching on quota attainment is undeniable. According to RevenueGrid, implementing a successful coaching program can increase average deal size, sales activity, win rates, and new leads by 25%-40%.

Today, a staggering 40% of managers admit to lacking the necessary coaching skills...

On the path to helpful coaching

Let's first identify what bad coaching looks like in day-to-day operations:

❌ Breathing down reps' necks to update Salesforce.

❌ Conducting pipeline review meetings as grilling sessions.

❌ Staying high-level and avoiding in-depth discussions on deals with reps.

❌ Neglecting recognition and motivation.

If this is your day-to-day experience, I'm sorry for you. Ultimately, these types of approaches hinder the creation of a trust-based environment and hinder sales.

Instead, effective coaching should involve:

✅ Investing time with reps to examine deals and strategize on unblocking obstacles.

✅ Being willing to participate in sales calls and provide feedback afterward.

✅ Not only identifying areas for development but also proposing actionable plans to address them.

✅ Recognizing and celebrating both individual and team successes.

The best coaches are the ones who show empathy, who aren't afraid to roll up their sleeves to be helpful, and who create a positive environment for collaboration.

Will AI disrupt coaching?

With the latest advancements in artificial intelligence, especially with large language models and semantic technologies, it begs the question: Can an AI coach match the capabilities of a manager?

AI can now digest vast amounts of information across your sales systems and combine it with publicly available sources to:

• Suggest a path forward on deals
• Identify best practices
• Write flawless emails
• Identify key stakeholders
• And much more

Not to say that an experienced sales manager can't do all of this, but he/she probably can't do it as quickly and accurately.

I imagine a world where individual sellers are supported by an AI coach: guiding them on their day-to-day decisions and automating a lot of menial administrative work.

Human managers can then rely on training sellers on building trust with prospects and using their EQ to close deals - something AI might never be able to accomplish... or maybe it will

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