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Coach Your Way to Sales Leadership Success: Best Practices from the Field

Sales Leadership Coaching Success - featured image

Successful sales leaders were once great salespeople. They know how to identify and qualify opportunities, progress them, maximize the revenue, forecast accurately and close the deal.

Today’s sales leaders require more than the above. To lead a high performance sales team and to achieve the team’s full potential, leaders must take on the role of cheerleader, coach, disciplinarian, physiologist and administrator. In addition, there’s a wide array of leadership styles such as Authoritarian, Coach, Democratic, Transactional, Transformational, and Bureaucratic.

Personally, I use coaching-style sales leadership in my daily life and have found it to be most effective to lead high performance sales teams. Here are some key ways coaching leads to sales leadership success:

Get the right players on your team

It starts with hiring the best, retaining and enabling them to perform at their full potential. It may sound obvious, but you’ll get the most success coaching if you hire people who are coachable.

The sales leader should be able to sit and discuss with the team to prioritize, plan and strategize. Empower the team and let them feel that they are the ones who are driving and making this happen.

A Coach-Style Leader works hard to identify the abilities of the team and strategize a plan that uses each team member’s strengths to maximize business results and help each member be successful. For example, if a team member excels is driving transformational deals then he/she should be allocated to large complex accounts to create multimillion, multi-year deals.

Coach your team to success

Development of people’s skills is another important step in this leadership style. The leader should be able to understand the individual development plans of each team member and work with them as a coach to develop each sales person to their full potential.

This involves providing feedback in both formal and informal settings, agreeing on current gaps, setting up appropriate goals and putting up a structured development plan. For example, some salespeople can be great at identifying and progressing opportunities, but they may lack closing skills. In this case, the sales leader should be able to deep-dive and help in closing the deal. In this process the sales person learns to close and develop his deal closing skills.

Ask powerful questions

In a coaching style of leadership, asking powerful questions helps the team find potential solutions to a problem. This approach builds confidence, develops the skills of the sales person, and helps them reflect on situations which ultimately makes them more self-sufficient. Involvement and ownership in decision-making boosts sales person engagement and ownership of a task.

Here are some questions managers can ask:

  • Talk me through the sales cycle. What are the next steps to close?
  • Is the budget approved? How much is the budget? What are the compelling reasons for the customer to buy now? Why can’t they wait and delay the decision?
  • Who are the decision makers? Did we meet them? When can we meet the C-level?
  • Did the decision-makers/CIO/CFO give a commitment to sign the deal? When can we get this commitment?
  • What is needed from the solution and presales team?
  • What is required to bring this opportunity forward?
  • How can I help? What’s needed from management?
  • What are the possible risks for this to close in a specific quarter? What can we do to mitigate the risk?

I also probe my team to think big by asking questions such as, “Can you think how we can help transform this specific industry/country/territory with the help of our technology solutions?” If the team can think big, they will believe in it and then will be able to achieve it.

📚 Read: Coaching Salespeople Into Champions: 3 Times to Step In (& How)

Follow a sales methodology

When your team understands their expectations, they’re more effective at getting relevant answers from prospects and customers. This helps us streamline the conversation to be effective.

I follow the MEDDPICC sales methodology:

  • Metrics: What are the hard numbers on the economic benefits of your proposed solution to the prospect?
  • Economic buyer: Who are the decision-makers with purchasing power to close the deal?
  • Decision criteria: What are the factors prospects use to make purchase decisions (e.g., price point, features, functionalities, consideration of competitors, etc.)?
  • Decision process: What is the decision process and steps to make the purchase?
  • Paper process: Series of steps being followed from decision to signed contract?
  • Identify pain: what are the pain points and problems that our solution will resolve?
  • Champion: Do you have a person who can be your advocate in influencing the decision?
  • Competition: Who is the competition and what’s the plan to win?

📚 Read: 8 Letters that Can Double Your Income: An Introduction to MEDDPICC

Deep dive on the things that matter

Leaders should empower the team to run the business day-to-day — but at the same time, they should have a firm grasp of what’s going on, both at a high and detailed level.

The best practice is to deep-dive using territory reviews, account reviews, top opportunities reviews, periodic performance reviews, and weekly forecast calls. The objective of the deep-dive is not to micromanage but to have the detail to know when to interfere and help the team to make progress and avoid failures.

Here’s how a successful, coach-style leader uses the following:

  • Weekly forecast calls: Discuss how to support and progress the opportunities. It should be attended by support teams as well
  • Customer focus calls: Regular meetings with CXOs of high-touch accounts, decision-makers, channel partners and important stakeholders.
    • To drive this behavior, I as a leader set a target to meet 1 CXO per day – i.e 50+ CXOs in Q1 of the fiscal year.
  • Collaboration meetings: Cadence with support functions such as business development, marketing, presales and channel to drive collaboration. The leader should be able to remove barriers for the sales team by making sure that they get timely and proper support from internal stakeholders
  • Transformational opportunities: Work with team members to identify 3-5 transformational opportunities with each territory, and identify deals to close in the current quarter and for next 2 quarters.
  • Healthy pipeline: Maintain the focus of the team, along with the sales development team, on building a healthy pipeline for long term (next 2-4 quarters) while delivering on quarterly revenue by closing forecasted deals. This discipline is critical for long term success.

Celebrate success and build a fun culture:

For a seller, winning and closing a deal is a major milestone and a significant achievement. This comes after a lot of effort and hard work. Celebrate the wins of the sales team, recognise their effort and let them feel that they are making a difference. This will help drive a winning culture and keep the team motivated.

Also, let your best sellers share their learnings with everyone else in the team. For example, imagine one of the salespeople in the team is doing great in prospecting and meeting economic buyers. Request this person to give a presentation on their winning strategy. What are they doing differently? Are they sending a specific message? This will help replicate good behaviors and help drive a culture of success.

Bringing it all together

In summary, the characteristics of the coaching leadership style are collaboration, empowerment, support, guidance and high performance. The sales leader should be able to maintain a good relationship with the team but should be firm on deliverables such as territory coverage, account relationship mapping, healthy pipeline, target achievements, linearity, forecast accuracy and growth (QoQ & YoY).

The best part of a coach style of leadership is that it can be effective for first-line management, second-line management and for senior-level leadership as well. It’s a leadership style that can scale and help create a high performance team to deliver success. If a sales leader hires top sales talent, puts up a sound plan and executes it flawlessly, then there should be no reason for the sales leader and the team to fail.

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