The Secret to Accurate Forecasting: Lessons from My 15-Year Career
Nothing gives me more eye twitches than not being able to forecast with confidence. While there’s always room for improvement, how do you move from being gut-based to data-driven in your forecasting?
Forecasting is a key business activity that drives countless downstream decisions:
If we sell X, we’ll need to hire Y more support, implementation, or other roles.
If we achieve plan, we can invest in new initiatives. If not, we may need to cut back.
Over the last 15 years, I’ve worked across transactional, mid-market, and enterprise sales motions. Here are lessons I’ve learned and actionable strategies to help you implement them in your organization.
Why Accuracy Lags
I’ve always had a target range for what “good” forecasting looks like:
Within 5%? That’s Great.
Within 10%? That’s Good.
More than 10% off? That signals room for improvement.
These are +/- ranges. For example, if you forecasted $1M but achieved $1.2M, congratulations… you overachieved! But it also indicates you didn’t have a strong grasp of what you could realistically land in the period.
Here are some common reasons accuracy lags:
1. Poor Sales Process
When teams interpret sales stages differently, alignment suffers. A well-defined, objective-based, buyer-driven sales process allows for productive deal conversations.
For renewals: Are you engaging with key accounts early enough to address churn risks? Or are you being surprised at the last minute when a customer declines to renew? Proactive engagement prevents costly surprises.
2. Poor Pipeline Inspection
Walking into pipeline reviews or forecasting calls with outdated or inaccurate opportunity data wastes everyone’s time.
Equip sales managers with tools/frameworks to assess deal health.
Align inspections with the sales process, ensuring sellers provide the necessary insights.
Create simple CRM views to identify issues like stalled opportunities, outdated next steps, or expired close dates.
3. Poor Pipeline Management
Overloading sellers with opportunities often backfires, leading to neglect.
Ensure reps have balanced workloads and enough time to focus on each deal.
Avoid the trap of focusing only on short-term closers while letting other opportunities stagnate.
4. Poor Operating Rhythm
A lack of structured operating rhythms is easy to fix.
Define meeting cadences and expected outcomes.
Reps should clean up pipelines before manager meetings. Managers should roll up their insights for leadership before the forecasting call.
Consider a rotating weekly focus (e.g., pipeline creation, next quarter outlook) and daily standups during the quarter’s end to track key deals.
5. Disconnected Tools and Reduced Visibility
Leverage tools to integrate activity data (meetings, emails, etc.) with opportunity data. Use them to track deal progression.
Conversational Intelligence tools add another layer of insight.
If your CS team isn’t managing renewals in the CRM, resolve that gap immediately.
6. Overburdened Customer Success (CS) Teams
If a CS rep is responsible for 100+ renewals in a quarter, things will fall through the cracks.
Automate where possible, especially for low-ACV accounts. For example, include evergreen clauses with CPI adjustments to reduce manual renewals.
Assign higher-value accounts to CSMs for personalized attention.
Key Learnings from My 15 Years
Forecasting improves with time and discipline. Here are the top strategies that have worked for me:
1. Clean and Consistent CRM Data
Define and enforce sales stage criteria (e.g., MEDDICC fields).
Keep CRM data updated before forecasting calls.
2. BI/Data Team Partnerships
Use your BI team to analyze forecasting history and performance trends. Pipeline snapshots hold a ton of value.
Supplement vendor AI forecasts with custom data science models.
3. Adopt Tools to Support Forecasting
Tools like Clari and BoostUp.ai can score deals, provide insights, and visualize pipeline movement.
Be aware of their limitations (ex: over-forecasting early in a quarter). Adjust accordingly for triangulation.
4. Leverage History and Data to Anticipate Risks
Two common risks stand out:
Concentration Risk: If a single account or rep owns a significant share of committed pipeline, any miss can have outsized impacts.
Pipeline Composition: If your pipeline skews toward new segments, regions, or earlier-stage deals, conversions may differ from historical trends.
5. Transactional Businesses Are Easier to Forecast
Hope I don’t get in trouble for this one. Transactional sales motions provide more data points (monthly vs. quarterly means I can get 12 data points in a year vs 4), making trends easier to identify. Identify the 2-3 key drivers of performance so you can get a sense of how well you’re pacing earlier in the month.
Forecasting Is a Journey, Not a Destination
Forecasting is challenging because sales is both an art and a science. As you move away from transactional motions, variability increases. However, with discipline and consistent effort, you can achieve the +/- 5% threshold of accuracy.
Start by assessing where your organization can improve, and take steps now to make those changes.
What have you found helpful in improving forecast accuracy? Let me know in the comments!
If you’d like to discuss how to enhance your team’s forecasting accuracy, let’s connect