Sales Coaching Tips After a Lost Deal

Your team just burned through a long sales cycle culminating with a tough loss to a competitor. Price wasn’t even the problem. Up and down the chain people are ticked off, left commission-less, and questioning their role. Your team needs a leader more than ever, so what now?  

How can you breakthrough the disappointment, take action from the loss, and get your team back on a productive track?

It’s important to facilitate great learning and empower your sales reps to develop, even after a disappointing loss. Think about your favorite sports team and how their coach handles losses. Pinpointing opportunities for improvement and encouraging critical thinking are crucial to improvement in sports, and in sales.

Choosing the right accounts, finding the right timing, and approaching a lost deal with the right sales coaching mentality are important factors in turning a lost deal into an organizational win. Follow this simple process to make sure you’re capitalizing on these critical moments.

Lost Deal Account Selection & Timing

The good news is that the most important coaching moments happen after the tough losses.

Start with pinpointing the moment the momentum turned. For most of you, that’s during the later stages in the sales process. Focus on what happened in the fourth quarter. Maybe it was a poor handoff, or a late follow up. Or maybe your team completely misread the defence. Whatever the problem, it’s your job as a sales manager to identify it at its root.

Once the problem has been identified, it’s time to address it, and address it fast. Coaching moments work best when delivered immediately after the problem. You wouldn’t punish your dog four days after peeing on the couch; coaching only works when it’s done in conjunction with the action.  Why? The human mind tends to reinterpret the past. Knocking out a lost deal analysis sooner than later will help yield a better and more accurate result.

One tip for making sure lost deals don’t fall through the cracks is to schedule regular review meetings with your reps. If you’re going that route, how often should you schedule meetings with your reps? That entirely depends on the length of your sales cycle.

If your sales reps go through deals and cycles on a monthly basis, a monthly check-in should be sufficient. If your sales cycle takes upwards of six months, you may plan on scheduling your meetings around the actual deal activity vs. the calendar.

The Sales Coaching Approach

Do the best teams only talk about their losses? No, they celebrate their wins too.

You don’t want your sales coaching system to only focus on the negatives. The point is to create a continuous stream of learning, and to help pick your team back up when they need it.

One way to communicate a neutral approach is to make reviewing lost and won deals a normal part of your sales culture and coaching program. Consider it a regular part of your post-game routine, whether you won or lost. If reps know it’s the ordinary procedure, they won’t be defensive or worried about negative repercussions.

Think you should single out your all-stars and weak links? Think again.

Don’t determine who gets sales coaching based on skill level. If newer reps see more successful reps going through the sales coaching process after major deals are lost, they’ll be excited about the opportunity to do the same. Including all of the reps in the process is crucial for success and better team development.

Regular training leads to 50% higher net sales per employee, so make the most of these opportunities by explaining your goals.

Sales Training Statistics
Source: American Society for Training and Development

Your strategic approach should be obvious. Explain to your sales reps that learning from lost deals provides an opportunity to share lessons and insight through sales coaching efforts for the entire team. There is plenty of benefit for everyone all around.

The Lost Deal Analysis

Think about what happens in the locker room after a loss. What approach has the biggest impact? Yelling? Sugar-coating? Watching back footage? Expressing how proud you are of them? Letting your team tell you where they went wrong?

One of the most important factors when starting the analysis, is making sure it’s a true sales coaching moment. Having the right attitude and amount of patience are critical.

To maximize the benefit sales reps can get through analyzing their lost deals, they need to do the brain work on their own. Calling them into a meeting and sharing your own opinions is a waste of your time, and theirs. Instead, let them review the footage and come up with their own ideas. Help the out by asking them the right questions to get them thinking critically on their own.

What are the right sales coaching questions to ask?

We’ve broken down some of the major categories when it comes to analyzing a deal, and questions associated with them to get you started.

Customer Analysis

Common customer analysis questions you might ask:

  • Was this a target customer?
  • Where they in need of the product or service?
  • Would the product or service work well for them?

Answering these questions will help your sales rep identify whether they were targeting the right type of prospective client in the first place. If they were, it’s safe to say the reason the deal was lost lies elsewhere in the sales cycle. If the weren’t, this will be a great opportunity for your sales rep to gain some insights into how they can better target future prospects.

Sales Process Analysis

Common sales process analysis questions you may ask:

  • What stage did they get to in the sales process?
  • How did each of the previous stages go?
  • Were there any signs the deal might not go through?

Taking a closer look at each stage of the selling process will help provide some insight for your rep as to what stages they excelled at, and where they need to improve. Analysis in this stage can also help identify unique customer needs by stage, providing important information to your organization as a whole.

External Feedback Analysis

In addition to analyzing the lost deal internally, you should seek outside data as well. Depending on the seniority of your sales rep you can choose to accompany your rep throughout this process, or to let them have the conversation with their customer on their own.

Common feedback questions you might ask a customer:

  • How many firms were involved in the proposal process?
  • At what point did you know our firm wasn’t going to win the deal?
  • Was there anything we could have done differently?

Remember, sports teams have coaches for a reason. Don’t leave your team hanging after a big game.

Instead, help your reps see their losses as an opportunity for greatness. As Michael Jordan said, “I’ve failed over & over & over again in my life & that is why I succeed.”

Using these three major areas of analysis with the right sales coaching mentality will help your sales reps turn negatives into positives. Your sales coaching efforts will help them close more deals by taking an introspective approach to their craft.

Do you have other successful sales coaching tactics you regularly use when one of your sales reps loses a deal? We’d love to hear about them.




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