Conquer the Complex Sale

Too often we leave salespeople out in the field to fend for themselves on some very complex and challenging high dollar deals with companies 10 to 100 times our size. Crazy, right?

In our organizations, we need to be clearer about the sales leader’s role in the complex sale. So here is what they need:

  • To clearly understand the complex sale and what makes it challenging.
  • To understand their role in moving the sale forward.
  • To learn how your coaching can lead to closing more of these complex deals.

3 Facts for Sales Leaders

  1. As the sales leader, you will always have a role in the complex sale.
  2. That role will change as your company grows.
  3. Conquering the complex sale requires strategy.

Clearly understanding the complex sale and what makes it challenging is covered in this BrightTalk and in this post. So, let’s focus here on understanding the sales leader’s role in moving the sale forward.

Who are the Sales Leaders?

As the sales leader, you may be the company owner, a senior sales leader or a sales manager. In every case, you have a role.

What is Your Role?

Managers spend time doing a lot of things that leave them little time to help their teams build strategy or coach salespeople to close deals. How many of you would say you spend 50% of your time on strategy and coaching? 80%? Imagine if you could spend more time coaching and leading strategy. How would it shorten your sales cycle? How many more deals would close?

3 Keys to Closing More Complex Deals

  1. Strategy – building strategies with your team to advance the sale.
  2. Positioning – Positioning all of the right people at your company with all of the right people at your company.
  3. Coaching – continually providing the coaching needed for positioning and strategy to advance the sale.

Essential Components of Your Role

  • Keeping the funnel full
  • Fully qualifying opportunities
  • Getting properly positioned
  • Education on the buying process

  • Managing timelines
  • Managing expectations
  • Developing strategies
  • Handling internal complexities

Coaching Can Lead to Closing More Complex Deals

Coaching is the key. You can train them to do strategy and positioning but without the continued coaching they won’t get the same results.

Questions You Can Ask when Coaching

  • What did you do to prepare for the sales call?
  • What was your objective for the call?
  • Who did you meet with?
  • What did you do to bring value and insight?
  • Where are they in the buying process?

  • What action did you commit to?
  • What action did they commit to?
  • What other solutions are they considering?
  • When will they make a decision?
  • What are the next steps?

Closing the Complex Deal

Let’s practice. Choose a real opportunity that is not already a done deal but somewhere in the process.

“I have the opportunity to sell Company Name, our Product Name(s), $ or #units for implementation on Date with a close Date.”

Current Position

  1. Who are the buying influences you know for this sales opportunity?
  2. How will our solution meet each of their needs?
  3. What other solutions have they considered?
  4. Who else will be involved in making the decision?
  5. What is the best way to include everyone involved in the decision-making process?
  6. What is their budget?
  7. On what factors will they make their decision?


  1. What is their timeline for implementation?
  2. What is their timeline for making a decision?
  3. Based on those two dates what is the close date the buying influences have agreed to?

Company Resources

  1. Is there anyone from your company you have involved or need to involve?
  2. Are there any resources you need to move this opportunity forward?
  3. What are your next steps?

Did I cover what I promised?

  • Clearly understand the complex sale and what makes it challenge – I hope you will go watch the BrightTalk if you haven’t already
  • Understand your role in moving the sale forward – What can you do to make sure you play your role?
  • Learn how your coaching can lead to closing more of these complex deals – I gave you some ideas, if you need more, please schedule a call with me.

Watch my BrightTalk, The Sales Leader’s Role in Conquering the Complex Sale if you want to get more information on how to close these complex deals.

About the Author Alice Heiman

Alice Heiman, the CEOs Sales Coach. According to, she is among the world’s leading experts on the complex sale. She strategizes with sales leadership and provides innovative ideas to grow sales. Originally, from the widely known Miller Heiman Group, Alice and her team incorporate the newest research and best practices to provide sales programs that generate immediate and sustainable results.

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