How I Ran a Team: a rhythm people can plan around, and a forecast that tells the truth

The short version

For most of my career I have carried a number and led the people who carry theirs. People ask what I actually did every week as a leader, and the answer comes with research that explains why it works.

• A team performs on a rhythm it can plan around: a weekly one-to-one with every person, and a weekly team meeting that runs in three parts.
• The research agrees that coaching is the highest-impact lever a sales manager has, and that most firms leave it to chance.
• Good coaching ends with the seller saying the answer, because the answer a seller reaches is the one they go and execute.
• A forecast tells the truth only when every deal in it is held to one standard: whether the buyer's own view of the problem has been surfaced and aligned to.
• The habit that protects the forecast most is killing deals early, and the seller has to be the one who makes the call.

1. The first leadership decision I made was about my own seat, and it set the rule for every team after it.

At Dimension Data I went to the CEO, told him I was tired of a model that rewarded mediocrity, and asked to move from hardware selling into the first services-only role. That seat became the foundation for Dimension Data's client partners. I start with it because it shaped how I led everyone afterward. People work to the system around them, and if the system pays the same for coasting as it does for the hard work, most of them will learn to coast.

So when I ran teams, I started with the system rather than the speeches. Motivation matters, and a good Monday call can lift a room, but without structure under it the lift is gone by Wednesday. What holds it, in my experience, is a rhythm the team can plan around. Every person had a weekly one-to-one with me and the whole team met once a week, while the forecast was built the same way every time so nobody had to guess what counted.

Exhibit 1 · The week the team could plan around

Predictability is the point of the whole design. A seller who knows the one-to-one is on the calendar every week brings the hard deal to it instead of hiding it until the quarter ends. Once the forecast is built the same way every week, nobody spends Friday negotiating it.

2. Coaching is the highest-impact lever a sales leader has, and it only works when it is on the calendar.

The weekly one-to-one was the center of the rhythm. Every person on the team got one, and we covered the same ground each time: their deals, their opportunities, the obstacles in the way, and coaching on each.

The research backs the habit. In a survey of 206 firms employing more than 500,000 sales professionals, the Sales Management Association found that managers rated coaching the most impactful sales-effectiveness investment available to them, ahead of training, technology and compensation. Most of those firms coached reactively. Their coaching effort went mainly to poor performers and to the people who asked for help, and their strongest sellers were coached least. High-performing firms coached 15 to 20 percent more, across every type of salesperson the study covered.

CSO Insights found the same gap from another angle. In its 2017 World Class Sales Practices study of more than 1,200 participants, as Jim Dickie reported it, 34.7 percent left coaching to each manager's discretion and another 35 percent coached informally. Only 11.3 percent ran what CSO Insights called dynamic coaching, a formal process tied into the CRM, and the structured approaches posted the higher win rates.

Coaching that depends on the manager remembering to do it turns into coaching the people who are already struggling, so the fix is to schedule it for everyone. In my judgment the top seller who never gets coached is also the one most likely to carry a stale deal, because nobody is asking them the hard questions.

3. The best coaching ends with the seller saying the answer out loud.

In the one-to-one I mostly ask leading questions, and I keep asking until the seller reaches the answer. That is slower than telling them. I do it anyway, because the answer a seller reaches is the one they go and execute. An instruction from me gets carried out at the level of an instruction, while a conclusion the seller arrived at gets carried out like a promise they made to themselves.

I want to be fair to telling. There are moments when a leader should simply give the answer, such as a pricing rule or a legal limit. Questions used as a ritual, when everyone already knows the answer, waste a seller's time and start to feel like a test. The flow below is for judgment calls, which are most of what a seller faces in a week.

Exhibit 2 · Coaching by question, step by step

Take a hypothetical new hire. Say a seller joins the team and is struggling in their first quarter. They are working hard and their calendar is full, yet nothing is moving. The temptation is to hand them a list of what to do. In the one-to-one I would do the opposite, and use each week to ask one question that moves them a step.

By the end of that quarter the seller may not have closed much. What they will have is a way of working they built themselves, and a forecast that is smaller and truer than the one they started with. Every decision in the right-hand column came from them.

4. The weekly team meeting had three parts, and the last one is where the team did its best thinking.

Once a week the whole team met, and the meeting always ran in the same order. It opened with updates from the team and the organization, so nobody learned about a change in the hallway. A guest came next, from another department or from a partner, so the team saw the company beyond its own territory and knew who to call when a deal needed help.

The last part was what I called Blue Sky: open collaboration in breakout rooms, with three or four topics running at once. People brought the problems they had not solved yet, whether a stuck deal or an idea for an account. During the remote years Blue Sky became the team's water cooler. Running several rooms at once also meant the conversations did not all route through me, which is how a team starts learning from itself.

Exhibit 4 · Anatomy of the weekly team meeting

If I ran it today, I would record the rooms, put the recordings through AI and send everyone one consolidated read-out afterward. The most useful part of Blue Sky was always the room you were not in, and a read-out gives that room back to everyone.

5. A forecast tells the truth only when every number in it rests on evidence.

The forecast is the one document every leader above you reads, and most of them do not fully trust it. Gartner's State of Sales Operations survey, published in February 2020, found that only 45 percent of sales leaders and sellers had high confidence in their organization's forecasting accuracy. Gartner also named one cost of that doubt: leaders chasing a quarter become more willing to approve discounts they would normally reject.

My forecast came from visibility. I could see every deal through Salesforce. The weekly cadence showed me the team, and staying close to the accounts myself told me when a number was hope rather than evidence. In the NTT cross-sell program we made that formal: an opportunity review board and a deal intake process qualified every opportunity before it counted.

Underneath all of it sat one qualification standard. I trained in SPIN at Huthwaite, MEDDIC and MEDDPICC, Miller Heiman and Challenger, and I inspect every deal for the same thing: whether we have surfaced the buyer's own view of the problem and aligned what we sell to it. A single standard makes a commit mean the same thing from every seller. When each seller qualifies by instinct, the leader ends up forecasting moods instead of deals.

Exhibit 5 · The forecast evidence ladder, from hope to commit

Gartner's own advice points the same way. It recommends building data-quality inspection into the recurring conversations between managers and sellers, and the weekly one-to-one is exactly that conversation. When the rung a deal sits on gets discussed every week, the forecast corrects itself in small steps instead of in one large miss during the last month of the quarter.

6. Killing deals early protects the forecast more than any other habit, and the seller has to make the call.

The hardest habit to teach was killing deals. A seller who has worked an account for months wants to keep it in the forecast, and a buyer whose view of the problem will not move can keep taking meetings for two quarters without ever buying. Carrying that deal costs the seller two quarters of time and costs the forecast its credibility. I would rather explain a smaller forecast that holds than a larger one that falls apart in the last month.

As a hypothetical, this is how I would handle it. Say a seller has carried a deal for two quarters and wants to commit it again. Telling them to drop it teaches nothing, and the deal tends to come back the next quarter under a new name. In the one-to-one I would ask the questions below and let the answers do the work.

If the honest answers sit in the right-hand column, the seller usually reaches the conclusion before I do. A deal the seller decides to kill stays killed, and the time goes to an account where the buyer's view and the offer actually meet.

7. The results came from teams that knew what to expect, and AI should make that rhythm cheaper to run.

I am careful about claiming that a meeting format wins awards. The market and the people on a team matter more than any calendar. What I can say is that this is how I ran the work, and the record that came out of it includes President's Club five times at Dimension Data and Top Region in the NTT Group in 2016, 2017 and 2018.

Three years running is the part I value most. One great year can come from a single large deal. A run of them comes from a forecast people trust and a team that knows where its time should go, which is exactly what the rhythm is for.

AI lowers the cost of running all of this, starting with the consolidated read-out from Blue Sky. A short summary of what each seller committed to in the one-to-one would let the next week open where the last one ended. What AI should not do is replace the conversation itself. A one-to-one is valuable because the seller says the answer out loud to someone who will ask about it next week.

8. What this means for first-line and second-line sales leaders

1. Put a one-to-one with every seller on the calendar, every week. Cover their deals, opportunities and obstacles, and coach on each. Coach your best people too, because left alone, coaching drifts toward whoever asks for it.
2. Ask until the seller says it. Keep telling for rules and limits. For judgment calls, ask leading questions until the seller reaches the answer, then ask what could break it.
3. Run the team meeting in a fixed order, and give the last part to the team. Updates first, then a guest from another department or a partner, then open breakout rooms. Let AI turn the recordings into one read-out.
4. Hold every deal to one standard before it counts. Ask whether the buyer's view of the problem has been surfaced and whether the offer aligns to it. If you run a large program, give it a review board and an intake process.
5. Second-line leaders: coach your managers on the same rhythm. The Sales Management Association found that senior leaders coaching their managers was the single most important thing a firm did to make coaching work. Run your first-line managers' one-to-ones the way you want them to run their sellers', and inspect their forecasts on the same ladder.
6. Make killing a deal a normal outcome. Treat an early kill as good judgment in front of the team. A forecast you can defend is worth more than a bigger one that falls apart late in the quarter.

None of this is complicated. It works because it is predictable, and every seller on the team knows when they will be coached and what counts as a real deal.

Sources

• The Sales Management Association, "Measuring Sales Management's Coaching Impact", research brief (206 firms employing more than 500,000 sales professionals, copyright 2008 to 2014): salesmanagement.org. Coaching rated the highest-impact investment, reactive coaching aimed at poor performers, 15 to 20 percent more coaching in high-performing firms, and senior leaders coaching managers as the single most important support activity.
• Jim Dickie, "Dynamic Sales Coaching Can Help Your Players (Sales Reps) Win", CRM Magazine, December 2017, reporting CSO Insights' 2017 World Class Sales Practices study of more than 1,200 participants: destinationcrm.com.
• Gartner, "Gartner Says Less Than 50% of Sales Leaders and Sellers Have High Confidence in Forecasting Accuracy", press release, 12 February 2020: gartner.com.
• Recognition (President's Club five times, Top Region in the NTT Group 2016 to 2018): Dimension Data and NTT records.