Forecasting is the bane of my existence some days, and I say that as a revenue leader who has been doing this for over thirty years. It is also one of the most important things I do. If I cannot tell my leadership, my investors, or myself where we are going to land the month, the quarter, or the year, I do not really have a business. I have a hope.
In this Master Sales Series episode of the Conquer Local Podcast, I wanted to pull back the curtain on the mistakes I have made, the pain points every revenue leader feels, and a cleaner forecasting approach I have landed on after talking to mentors and digging through a lot of research. If you are running a sales team or you are the founder wearing the revenue hat, this is for you.
What a Forecast Actually Is
A forecast is not a guess. Your leadership is going to ask where you will end the month, the quarter, or the year, and you need proof points behind that number. In the early days of my career, I could pound the pavement, do the hard work, and magically show up on the last day with my number hit without really knowing how I got there. That does not scale. No one is going to fund your startup if you cannot put real dollars around a forecast, and your sales team will just bounce off the walls without one.
The Pain Points Every Revenue Leader Feels
Here is what forecasting pain looks like in practice, because I have lived every one of these:
- Realizing you do not have a forecast, or you cannot trust the one you have. The pipe is not full enough to cover the commitment you made, and now you have to call a bunch of meetings. And meetings suck. If I get invited to one more meeting with no agenda and no clear deliverable, I am going to scroll to the bottom of a social app out of sheer disengagement.
- Spreadsheets from hell. Excel overload. I have a young gentleman on my team who, every time I ask for data, sighs because it is another manual process pulling him away from customers. If we had a proper forecast with science behind it, think of the hours we would save.
- The line by line. Interrogating every rep on every opportunity in their book. I have done this to millions of reps over the years, and recently somebody did it to me. They asked me to walk through twenty-seven deals I had brought across the line, and I was embarrassed that I could not speak confidently about two of them. It came back to bite me because I did not have a forecast I trusted.
- Putting your number out there and quietly wondering if you can deliver it. Every revenue leader knows that feeling.
The Three Forecasting Personalities
I have talked on this show before about the personalities of salespeople, the landlord and the cynic. Forecasting has its own set of personas, and most of us fall into one of three:
- The Sandbagger. Commits to $20,000 and magically delivers $40,000 at the end of the month. That is not a win anymore. It signals you either do not understand your book of business, or you are hiding opportunities to protect yourself. Investors are now saying a proper revenue organization has to come in within a tight percentage of forecast.
- The Sharpshooter. Hits the number every month. I respect this persona because it means the rep is putting in the work to interrogate opportunities and truly understands their line of business. The only risk is playing it too safe.
- The Optimist. This is me. Someone asks how much I can deliver this year, and I blurt out $2.8 million without stress-testing whether the pipeline can actually support it. Then it comes back to bite me because it looks like I cannot forecast to save my life. You can sometimes negotiate your way out of optimism if you are outperforming last year or hitting the investment thesis, but none of these personas except the sharpshooter is where you want to live.
As I put it in the episode: “Being a cowboy, just going out and doing deals and shooting stuff and bringing it back to the ranch, as you get bigger, that is not going to work. You can actually get bigger quicker if you have some processes.”
Why the Old Probability-Weighted Pipeline Is Broken
For years the CRM standard was to assign a percentage to a deal. This is 10 percent, this is 50 percent, this is 99 percent. I have moved away from that. Big credit to our CMO Jeff Tomlin, who dug in on this with me. Instead of arbitrary percentages, we tie the stage of the deal to what the rep actually did. I did not move it to 50 percent because I needed to fill my pipe. I moved it because I presented to the customer, sent the NDA, received it back signed, sent the credit app with a proposed contract, and the buyer came back asking for a proof of concept or red lines on the agreement.
Those are buying signals. If you know a large deal takes five presentations and you have given two, that deal is not ready to move to the next stage. That is the discipline.
Stop Making Excuses. Take Ownership.
One of the biggest pivots in my career was deciding to stop making excuses. There is a difference between excuses and ownership. Walking into a forecast review and saying, “Here is why we missed,” is an excuse. Walking in and saying, “Here is why we missed, here are the three things I am changing in our sales process, and here are two deals I already moved because of those changes,” is ownership. Leadership remembers the difference.
My New Forecasting Approach: Five Things That Actually Work
After talking to five mentors and going through about fifty different places where I was screwing this up, here is the simple approach I use now:
- Be connected to real-time data. Your reps need to be writing into a system of record where the deal actually sits. As the revenue leader, you have to be involved in building out the stages of that pipeline. I like the MEDDIC approach, where each stage is measured against concrete criteria, not a gut percentage.
- Have intelligence built into the forecast. Account for historical seasonality. If every buyer goes on vacation the first two weeks of July, do not tell me you are growing July by 40 percent. If December has ten selling days and half your team is hungover, do not forecast a 200 percent lift. Factor in rep variability too. New reps do not ramp in 30 days.
- Build in efficiency. You need to be able to re-forecast at the drop of a hat. The economy shifts, your top seller goes on leave, you lose a major account, and you have to adjust. Quick pipeline reviews make that possible.
- Be informed without daily rep interrogations. I should not have to sit across from every rep and do a line by line to understand where we are. That should happen once a month, once a quarter, or when something big changes. I need to be able to check the number while I am on the bike doing morning cardio or sitting in the dentist waiting room.
- Demand reliability. The days of the cowboy are over. Your investors, your board, and your team expect forecasts they can trust. Your job is on the line to deliver that.
A Real-World Example
I sat with a young couple recently who had just launched a business. They were great at filling the top of the funnel. When I asked what training their reps went through, what the stages of the pipeline looked like, and how deals were tracked, the answer was a shrug. The founder admitted that when his wife pitched in the showroom, she stumbled, because there was no process for her to lean on. No one on that team could build a forecast, because there was no intelligence underneath it. That is where most growing companies get stuck.
Where to Go From Here
If you want to go deeper on the ideas connected to this one, Donnie Dye had a fantastic episode on quotas and how they tie directly to revenue attainment. Sam Jacobs had sharp takeaways on forecasting. Butch Langlois delivered a great breakdown of pipeline and forecasting discipline. All of those build on what I just shared.
The Takeaway
Forecasting is not about covering your ass. It is about building a revenue motion investors trust, a sales team that knows where they stand, and a leader who can look at the numbers and know what is real. Be connected, be intelligent, be efficient, be informed, and be reliable. That is the whole game.
If you are a revenue leader wrestling with an unreliable forecast right now, pick one of those five things and fix it this week. Then pick another next week. That is how I climbed out of it, and that is how you will too. Find me on LinkedIn and tell me which one you tackled first.