We’ve all been in the meeting. It’s a standard deal review. The manager sits with the seller, both looking at the dashboard, rather than each other. The are reviewing the deal, MEDDICC steps checked off, process being followed. Maybe a few questions about what the customer is saying, and how the salesperson is handling things. Some updates are made in CRM. Perhaps, next steps are agreed on. 30 minutes, the meeting is over. The manager goes back to the dashboard; the seller goes back to spraying and praying.
A status review.
What did the manager learn? What did the seller learn? Was anything accomplished other than checking the box for a completed review?
Let’s focus on managers, their jobs, and developing judgment. Since Sales Manager Survival Guide, I’ve been preaching “the leader’s job is to maximize the performance of each individual and their team.”
Too many seem to have drifted from this principle.
Over the years, in the spirit of helping managers, they have been given more data, dashboards, metrics, methodologies, processes, forecast calls, AI recommendations. All of this was intended to help them manage better. All focused on delivering more predictable results.
Simultaneously, scaling expectations grew, churn and replacing people took time, spans of control increased. The work skyrocketed.
And slowly, unconsciously, this changed the way managers spent their time. Where they had originally spent time with their people, understanding what was happening, helping them achieve their goals, and developing their people to improve their performance. That time got squeezed out.
Rather than understanding what was happening, why, and figuring out what to do, the job changed to focus on inspection and compliance.
The deal review which used to be discussions about how to win a deal became the inspection outlined above.
And this rippled through all levels of management.
Going back to the deal review, what is missing is ”What should the seller be doing next? What should the seller be doing to more effectively engage the customer, helping them navigate the buying process to confidently making a decision?”
This is where judgment starts. And it starts with the manager.
The dashboards tell us what is happening. The manager has to figure out what it means. Why is this happening? What happens if we do nothing? What should we change?
This is the moment I identified in “Judgment Starts Where The Analysis Runs Out.”
There are several aspects to judgment that managers have to develop. One is about the work. The second is about their people. The third is about themselves
The judgment about the work focuses on strategies, priorities, organization, people, process, tools, programs, investments, and, always, risk. It’s constantly reexamining, “What’s most important now?”
Some may require major shifts, some are tweaks, some are no change necessary. But each focuses on work.
Managers make judgments about their people. It focuses on how well each person is doing the work. A key question in looking at this is, “What does this person need from me right now?” Dashboards may give clues but not answers.
I’ve commonly used the example, Dave and Charlie have similar territories, quotas of $10M, pipelines of $5M. Charlie has a 40% win rate, Dave has a 20% win rate. What should you do with each. Based on the dashboard, they look very similar, but they are very different.
The judgment the manager exercises recognizes these differences, determining what coaching Charlie needs and what Dave needs.
Managers fall into traps, confusing compliance with judgment.
Compliance doesn’t build judgment. It is based on past judgments, not reexamined and improved. It’s strictly, “Follow the rules, Update CRM, hit your outreach goals, build your pipeline…..” It recycles what we have always done.
But compliance doesn’t identify or address the underlying issues or the changes that are happening.
One of the most important areas of judgment in working with their people is, “What is most helpful now, what is not?” We are sometimes tempted to give our people the answers, but one of the most important judgments a leader might make is knowing when they should let go and let the person figure it out.
So how do managers build better judgment. The process is exactly what I’ve outlined in prior articles. But let’s go deeper into two areas, developing judgment about the work, and developing judgment about how their people are doing the work.
Judgment about the work is really about the business. At senior leadership levels it may be about overall business strategy, markets, growth opportunities, current and emerging competition, global economics and disruption, organization, resources, investments.
At a mid-management level, it might be more focused on execution and operation. It might be the overall organizational structures, workflows, programs, processes, training, tools, roles/responsibilities, and metrics.
At lower levels it’s about team performance, getting the support they need, hiring, onboarding and so forth.
At all levels managers and leaders exercise judgment about the business. The scope and consequences are the only difference.
At every level, there are fundamental questions. What are we trying to accomplish? What work actually matters? What should we stop doing? Where should we focus? What resources are needed and how do we allocate them? What gets in the way of the work, what helps? What should be standardized and where do we need flexibility? Where do automation and AI fit? What risks should we take, what tradeoffs should be made? What needs to be changed because the world is changing? What assumptions are we making that are no longer valid? How do we engage our people in understanding, owning, and executing the changes?
As with any judgment, there is uncertainty. There is never a right answer, instead there is our best estimate. At the organizational level there are more complex tradeoffs, different risks. And part of judgment is that we may sometimes be wrong. We learn from this for future judgments.
At the people level, the judgment focuses on individual, each individual in the team. One of the things the effective leader does is to leverage their collective experience of working with the team. Each individual may see and strategize 10 deals, but in a team of 8, the manager gets to see 80 deals. Each individual is developing their judgment over the 10 deals.
The manager has the opportunity to develop judgment faster because they are learning from the experiences of the team. The simple math of what sellers see in developing their judgment and what the manager sees provides a tremendous multiplier effect. As I work with front line managers, I see a tremendous acceleration in their development, simply through the exposure to this broader perspective.
We see the continual looping. Managers work with each individual on the team. They gain experience through that and looking across the team. In turn, this translates into how they work with each individual.
There is an awkward paradox that underlies everything I’ve talked about up to this point. Maximizing today’s performance may degrade the organization or individual capability for next year. Effective leaders weigh both. They may focus on the near term, recognizing it may have an adverse future impact.
But the moment leaders fail to look at the balance, make the tradeoffs, instead constantly focus on the short term, they have made the decision the organization will fail in the long term.
And this, often, represents another paradox, that of self-orientation versus the business or the people. The manager who steps in to win a deal is maximizing for short term results and his own success, but potentially at the cost of developing their people’s ability to win the next deal.
Let me pause here for a moment. While it may be difficult for each of us to admit, so much of what we do is self-oriented. “How will my manager react? How will this impact my career? My comp, my performance evaluation?”
Self interest will never disappear. The key is “does it compete with or integrate with the interests of the business and people?” Stepping in to win a deal means you make your number, but it does nothing to develop the person’s ability to win the deal themselves. Providing the forecast you manager wants may make your manager happy, but it keeps you and the manager from understanding the real challenge and addressing it.
Aligning your self-interest with the interests of the organization and your people is critical for the organization, your people, and your success.
The paradox leads to a final critical thing in leaders developing their judgment, whether that focused on the work/organization or on their people, is knowing when the best judgment is to let go. Sometimes the greatest learning comes through failure. The key issue here is recoverability.
Leaders don’t protect people from every failure. They exercise judgment about which the organization and the people can afford and recover from. In doing this, they build their people’s judgment.
The failure of any single deal, any single program, any single new initiative is seldom catastrophic. Missing a quarter is usually not catastrophic. We don’t purposely look to fail, but it’s through these failures we learn, grow, and develop our judgment.
Now as I wrap up, what does all of this mean to managers and leaders today. I’ve claimed that many delegated judgment to their dashboards, to AI, to others making decisions for them.
What does it take for them to recover and own this for themselves?
First, we have to recognize we’ve delegated our judgment to these surrogates, things like our dashboards and AI. This has happened to all of us, unconsciously, we’ve surrendered more of our decision making. It’s simply a matter of recognizing this.
I’m not negating the power of the dashboards and tools, but these are the starting point, not the end. As I’ve said, judgment starts where the analysis ends.
In reclaiming and developing this, we begin by reclaiming the real work of managers and leaders.
Engaging in the work develops your judgment about the work.
Asking your people what they see develops their and your judgment.
Visit your customers and suppliers to understand what they are seeing, their challenges develops your judgment.
The higher your level, the more important it is to start looking inside and outside the organization to learn, expanding your thinking and developing your judgment.\
The higher the level, the more deliberate leaders have to be in seeking a diversity of experiences from which they develop their judgment.
These things are what the job has always been about, not additions to what you think you are doing.
Experience alone is not what builds judgment. It’s the mindsets and behaviors we bring to each experience that determine what we can learn from these experiences.
I’ll dive into this in the next post.
Afterword: I continue to be amazed by the quality of this AI based discussion. Other than a few mispronunciations, the ideas are stunning.
