Mandatory project management bootcamp for sales reps? Absolutely. When I transitioned earlier in my career from management consulting into my first sales leadership role in industry, I first asked each sales rep on my team two simple questions: “what’s your plan?” and “are you on schedule?” Often, I didn’t like what I heard.

The questions, of course, suggested that there was a sales plan. Too frequently, there was none. Or nothing I could recognize as a well-thought-out, measurable, deliverable-oriented plan—something that had been drilled into me as management consultant. Everything in my world had clearly defined goals, work tasks, schedules, resource assignments, deliverables and a budget; in other words, a project plan.

At the same time, I noticed that the sales reps most successful in hitting their sales targets had adopted some form of a project management approach to pursuing business. And I have seen this over and over again across multiple industries in my subsequent sales management roles and now again as a consultant to senior management.

In this Brief, we highlight the key elements of disciplined project management that can help sales people be more successful; that is, a project management bootcamp for sales reps. While sales reps need not be certified project managers, they can learn a lot from those professionals. We also suggest actions that sales team managers can take to instill a project management mindset in their people.

Project management bootcamp

At any given time, a sales rep will be juggling multiple sales pursuits, each at various stages of execution. These projects span a sales rep’s responsibilities from targeting customers, qualifying leads, crafting the value proposition, and selling the customer, to closing the deal. Some will involve only a handful of tasks and a few hours or days of effort, while others, such as responding to a complex RFP, may take months and involve a huge commitment of cross-functional resources across the company and even external partners, with multiple milestones and interim deliverables. Whether simple or complex, sales pursuits can benefit from disciplined project management.

Sales plan basics

  • Objective. While winning the deal at hand is the most obvious objective, successful sales reps seek broader and more strategic objectives. For example, to win the deal and convert a client “blocker” into a “supporter.” Or to add a national master service agreement to the business relationship. Or close the deal in the C-suite rather than in the procurement department.
  • Task definitions and deliverables. What will be needed to win the business? Beyond the basics of preparing an RFP response or simply quoting the business, these tasks typically encompass creating the value proposition, designing the solution (for example, people, process, IT, partners, implementation), pricing, mapping and developing relationships, and selling. And what are the specific deliverables for each task? Without clearly defined deliverables, task resourcing and budgeting are only guesses, putting the entire sales pursuit at risk. Do some tasks require deliverables from another and are they dependent on those tasks being completed before they can begin?
  • Project team. What resources are required to execute the tasks? A successful sales person knows the limitations of being a “lone ranger.” They build and manage a cross-functional sales pursuit team aligned to the needs of the plan. Team members don’t just design solutions or prepare pricing, they also can be tasked to reach out to their functional counterparts in the customer organization, say IT to IT, to validate the technical solution and convert these decision influencers into supporters.
  • Timeline. “Is the sales pursuit on schedule?” is one of the simplest questions to ask as a sales team manager. Missed deadlines—or the lack thereof—can jeopardize the pursuit not just in terms of getting a proposal out the door on time, but it can undermine its probability of success. Building a project timeline takes sales experience, clear definition of the tasks and their deliverables, and an understanding of the task dependencies. Prudent buffers can be built into the timelines to manage uncertainties.
  • Budget. The simplest sales pursuit plan needs a budget even if it is just an estimate of the sales person’s own hours over the project timeline. Other more complex sales pursuits may involve internal cross-charges for solution engineering services, for example, or external services.

As a sales manager, I often would hear from my sales reps, “I don’t know enough about the business opportunity or the prospective customer to draft a plan,” to which I then would ask, “then what’s your plan to learn more so that you can?” In other words, in my book, there is no excuse for not having a plan.

Managing the project

Some basic approaches can keep the sales pursuit moving forward per the plan toward a win.

  • Alerting.Is the project on plan? Weekly red/yellow/green tracking of project milestones and budget is often enough to keep both the sales rep and his/her manager abreast of the project’s status. No need for time-consuming project update meetings when the status is “green”; that is, on plan.
  • Critical path. Which tasks should be given the highest priority? Since a delayed task on the project’s “critical path” will delay the entire project, priority must be given to tracking and resourcing these tasks. Understanding task dependencies sharpens the rep’s ability to focus on these critical tasks.
  • Go, no-go check-points. Should the sales pursuit continue? Sales pursuit plans should include periodic checkpoints at which time the probability of winning and, for costly sales pursuits, the effort’s ROI, particularly compared to other sales opportunities in the pipeline that may be competing for the same project resources, are reassessed. Here the three key decisions are to: 1) continue as planned, 2) adjust the plan, or 3) terminate the pursuit and redeploy resources to more attractive sales opportunities. Sales personnel are often reluctant to terminate a sales pursuit, especially when they consider all the time and effort they have put into it. But these sunk costs have no bearing on the decision to continue or not.


The major CRM (customer relationship management) software solutions like Salesforce or Oracle CRM offer embedded project management tools. These are designed around the core needs of a sales pursuit, account planning, and other sales action plans and link to the broader set of CRM tools and data within the platform.

Specialized project management software applications like Microsoft Project offer even deeper functionality. However, even basic spreadsheet-based task lists and timelines can be effective for documenting the plan and managing against the milestones, and for easy updates. For more complex sales pursuits with a large number of tasks and task dependencies, CRM-tool based planning apps or specialized project management software are the tools of choice.


Sales managers should:

  • Assess the current practices within the sales organization as the starting point for understanding the changes required.
  • Establish a sales pursuit process incorporating a project management approach.
  • Provide the sales reps with project management tools, such as CRM-based, standalone packages, or spreadsheet templates.
  • Provide training and coaching to enable the sales reps to benefit from these project management processes and tools.
  • Monitor and manage sales reps and their sales pursuit projects against the plans.
  • Add professional project managers to the sales team for very large, highly complex sales pursuits.

Instilling a project management mindset and skillset in the sales force will increase win rates and improve the allocation of scarce resources to the best sales opportunities. It starts with asking simple questions of your sales reps and providing them with the processes, training, and tools to answer them clearly and succinctly: “Yes, we are on schedule, on budget, and intend to be successful.”

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Dave Frentzel is a partner at New Harbor Consultants. Dave brings 30 years of management consulting and hands-on executive leadership experience to improve business outcomes. Prior to joining New Harbor, he held various senior positions at 3PL and supply chain technology companies. Dave has extensive global management expertise, having lived and worked internationally. He helps companies with their global go-to-market, organizational, sales, sourcing, manufacturing and supply chain strategies and operations.