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7 Most Common Mistakes When Annually Planning Sales

Planning has two main approaches. Let’s call them proactive and reactive planning.

  • Proactive planning = building new policies, strategies and initiatives.
  • Reactive planning = monitoring and iterating based on results.

Good sales plans include both. They account for hurdles in implementing new initiatives and track the right data needed to evaluate rep performance, addressable market, and initiative value. 

Great sales plans go one step further. They approach planning as a constant process of monitoring, reviewing and adapting. Like a workout, they increase the strength and flexibility of departmental activities through repetition. Then, they add tweaks to routines to course correct for the best results. 

To grow your sales plan from good to great, check out the seven most common mistakes in sales planning. Address them to improve efficiency, maximise revenue, and reach your goals. 

The 7 most common mistakes revenue leaders make when annually planning sales:

It’s a classic human oversight made up of two components:

  • Our inability to accurately assess how long things will take ahead of time (the planning fallacy
  • Thinking we can control more of the process than we can. 

The most diligent and prepared revenue leader will still have to contend with external events, market forces, and issues around execution and adoption. When planning, you need to build in flexibility or regularly review your strategy. Focus on “planning to be agile and being prepared for whatever might hit you,” advises Mark Truman, Chief Revenue Officer at EdgePetrol

Control what you can, but be prepared to flex and adapt to what you can’t. 

Sales planning during an economic downturn is tough, sure. But it’s not insurmountable. The key is to take a clear-eyed look at your company and market situation. 

Play to your strengths by prioritising areas you’ve seen success in previous years, and cut back on weaker areas. Perhaps one territory is a sure bet, but with closer attention could yield higher attainment.

Stuart Dale, VP of Revenue at Screenloop, gives the example of seasonality. If you are strong in a specific market in the spring, prioritise allocating resources then instead of during weaker seasons. 

Go too big, and you won’t get up and running until well into Q2. However, playing it safe and just tweaking what you’re already doing can leave huge opportunities on the table.

The key here is discernment:

  • Weigh up high-growth opportunities with rollout logistics
  • Consider how recently you introduced significant structural changes
  • Assess potential impact against business readiness.

Remember to sync up with product leaders and take the time to align with marketing. Sunne Kumaar, Global VP of Sales at ServiceNow, recommends looking back over the last 3-5 years for patterns in what is and isn’t working when planning a significant revamp.

The greater the change, the longer it’ll take to successfully get up and running. 

“Change control management is key,” says Nick Ellis, SVP Emerging Markets and Field Operations at Progress. With a system lag all but inevitable, you’ll need to build ramp-up time into your plan. Nick recommends close attention when issuing new territories and accounts, reassigning pipeline, and evaluating deals.

Some other common blind spots: 

  • Have you factored in the time it takes for new demand-generation activities to impact your pipeline? 
  • Should reps focus on closing, or would Q4 training improve rollout? 
  • If you’re making territory or account changes, do you have a holdover plan? 

It’s no good having a winning strategy if teams can’t execute it. For each initiative, you need to know: 

  • How teams will be incentivized. What are the details of compensation plans for each role? What behaviour will these encourage? 
  • If teams will need new tools or training. If so, does your plan allow for ramp-up?  
  • How territories, accounts and leads will be allocated. Does your current tech stack support your plans? Can activities be tracked accurately

Michael Boardman, Director of Revenue Operations at Riskonnect, admits he typically sees comp plans being finalised into Q2. “We spend so much time focusing on the metrics and getting alignment on GTM strategies,” he says. “We always seem to run out of runway”.

Try to reduce noise and simplify as much as possible. With comp plans, for example, you want reps to see the direct correlation between their output and compensation.

“A plan is nothing if you can not get your team behind it,” says Dan Richardson, GM, North America & VP Revenue at EdgePetrol. If you’re making significant changes you need to create champions within each department. Effective communication ensures your team understands why changes have been implemented, how they can succeed, and what training will make the goals realistic.  

Kimberley Haley, VP of Revenue Operations at Talend, recommends the ADKAR model for communicating new initiatives or changes. It covers the five areas individuals need to feel empowered to adopt a new system: Awareness, Desire, Knowledge, Ability and Reinforcement. 

Namrata Ram, VP of Sales and Strategy at Slack, says a crucial element of annual sales planning is ensuring you have the right tools to do the job. 

Does your current technology enable you to confidently assess rep, territory and team performance? If not, how can you be sure you’re effectively planning for the best growth opportunities going into 2023?

Be aware that innovations happen constantly: you might not know how much the market has changed since your last annual sales plan. Take the time to understand if big-picture changes could transform your prospecting, CRM use, and forecasting accuracy.


So there you have it. Looking for success in 2023? Factor in the 7 areas above for a robust and flexible sales strategy.