Coaching Salespeople into Sales Champions

coaching sales people

By Keith Rosen
Review by Jennifer Dawson

Management is dead.

Keith Rosen admits it’s a bold statement, but it underlies his innovative approach to creating sales champions and is certainly a thought-provoking sentence to slide into the opening chapter of his book.

Since Rosen isn’t advocating for flat organizational structures or axing all sales management positions, it might be more accurate to say that management is on life support. The prescriptive, problem-focused, and punitive approach of traditional management, Rosen asserts, is failing today’s salespeople. Enter coaching, which Rosen defines as “the art of creating new possibilities.” Coaching’s collaborative, creative and solution-focused approach, while not a quick cure for managerial ills, promises to breathe new life into any sales department.

Rosen spends a significant amount of time outlining the principles of coaching, the qualities of a “masterful coach”, fatal coaching mistakes, and describing traditional managerial approaches and why they don’t work. The key learning from the book, however–and this is where Rosen pens his second memorable phrase–is his assertion that “the question is the answer.”

Why questions? In the role of coach, a sales manager engages in meaningful one-on-one conversations with salespeople which correspond to the 80/20 rule: 80 percent of the talking is done by the salesperson, and 20 percent by the coach. In order for this to happen, the coach spends most of his or her time asking insightful, solution-focused questions and listening carefully to the answers, which invariably become the basis for further questions.

It makes sense, then, that Rosen’s book is packed with examples of illuminating questions (including an appendix full of one-sentence gems). It’s a long book, but chapter 9 (“Facilitating an Effective Coaching Conversation”), chapter 12 (“Develop an Internal Coaching Program”) and the question-loaded Appendix are worth a careful read.

It can be difficult to reconcile Rosen’s advice to focus a coaching session on the salesperson’s values, goals, and needs with the fact that the financial viability of a company depends largely on meeting and exceeding externally-dictated sales targets. The case studies, which consist of pages of realistic dialogue between salespeople and their managers, are particularly useful here. It is clear that, while the questions a manager-as-coach asks are designed to call forth the innate creativity and resourcefulness of the salesperson, the questions remain focused on practical, sales-oriented issues. The difference between a traditional management approach and a coach approach lies, not in the subjects under discussion, but in the way these subjects are approached and the place where the answers are found.

Rosen’s advice includes the following:

  • Suspend assumptions and judgment. Be curious instead.
  • Listen carefully. Reflect back what you are hearing. Listen for what the person is saying–and not saying.
  • It’s not about you. Remember that you’re teaching your salespeople to think independently and identify their own solutions. The conversation should focus on what they value and need, not what you value and need.
  • Don’t work too hard. If you feel drained after a coaching session, then you aren’t asking enough (or the right) questions.
  • Ask permission. Permission equals buy-in. Don’t assume that coaching is appropriate or appreciated by every salesperson or that a salesperson will say “yes” without a sense of connection, trust, and a belief in the value of the conversation. Once your salesperson has agreed to be coached, ask permission before posing a tough question.
  • Coach with your heart, not your head. Use your intuition. Create a safe space for you and your salesperson to be vulnerable. Vulnerability is risky, but without it no one will accept responsibility for mistakes or commit to improvement.
  • “Coach the gap.” Identify the stories, excuses, mindsets, and assumptions that are holding your salespeople back and help them explore the impact these have on their performance. Coach them to reach a goal they identify for themselves.
  • Follow a consistent format. Start by having your salespeople fill out a coaching prep form. Ask questions, listen, discuss, and support your salespeople. Have them identify the value of the session, their action steps and fieldwork, and how they are feeling at the conclusion of the conversation. Schedule the next meeting.
  • Get your own coach. Your own assumptions and beliefs will invariably influence your interactions with your salespeople. Get clear on your goals and needs as a manager so that you can best support your staff.

One of the most compelling benefits of a coach approach to sales management lies in the transformative power of questions. By asking insightful, non-judgmental, and revealing questions, a sales manager teaches his or her salespeople to ask these kinds of questions of themselves and, ultimately, of their prospects and clients.

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