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You're In Good Company

CEOs, GMs, company Presidents, Board Directors and senior marketing and sales leaders often wrestle quietly with questions about strategy, markets, sales and marketing. 

Strategy & Board Operations

  • Do we have the right revenue growth expertise on the board/in our skills matrix?
  • What competitive threats are likely to emerge in several years, particularly from alternative solutions?
  • What technology threatens our business?
  • What trends are likely to weaken / strengthen competitors?
  • Have we properly defined our ICP for our strategy?
  • Are pricing and product roadmap properly aligned with strategy?
  • What should we be doing now to prepare for succession? Exit?
  • What acquisitions should we consider?
  • Does our return on equity justify the hassles?
  • What leadership will we need to plan for in succession to meet growing market demands?
  • Is the executive team capable of driving predictable revenue growth
  • Do we deliver buyer experiences commensurate with market expectations?
  • If the economy is in a recession, will we still sell as much? enough? 
  • Are our marketing and sales teams as "world-class" as our manufacturing?
  • Are we too reliant on existing customers for revenue?


  • Why don't we get more leads? How many leads should our website generate?
  • How do we get more leads?
  • Why don't we sell more of the leads we receive?
  • Should we do more social media?
  • How can we create more content? What content should we create?
  • How important is SEO? Is ours good? What results should we see?
  • How much should we spend on marketing?
  • Is our website effective? Is our traffic appropriate?
  • What should our email marketing include?
  • Are we in the right trade shows? 
  • What is our return on marketing spend? Why don't we know more accurately?




  • Do we have the right sales leaders and managers?
  • Do they have any blind spots? How would we know?
  • What management coaching do they get?
  • Who/what are they accountable to?
  • What metrics do you use to measure them?
  • Do they coach enough?
  • Is our span of control (number of reps/manager) appropriate?
  • Should managers carry quota?

Sales reps

  • Do we have the right people? Right number? Right roles?
  • Why do so many miss quota consistently?
  • Do we believe they can get better?
  • Does our team have the capacity to improve? Sell more? Improve margins? Gain market share?
  • Who would have to change in order to improve?
  • What percent of our people really have fire in their bellies?
  • Are our reps proactive? or reactive?
  • What's preventing them from being proactive?
  • Why are we so frustrated with our sales team?
  • Which of our salespeople will continue to sell successfully in a recession?
  • Do the reps have clear activity and accountability expectations? Are they meeting those expectations?
  • What's keeping them from doing more?
  • Is everyone on the team held accountable?
  • What's the potential of each of our reps? How many are hitting that?
  • How can you measure their individual strengths and weaknesses?
  • Is customer service considered sales?
  • What are the most common reasons/justifications/excuses you hear from sales why they don't bring in new business or hit quota?

Recruiting & Hiring

- why is turnover so high? - why do so few sales candidates work out - is our onboarding adequate? - where do we make hiring mistakes? What part of the process is at fault? - do we know how to improve recruiting and hiring? - if your top sales person resigned today, do you know how you'd replace him/her? - how long between starting to recruit and having a new rep revenue positive? what's the cost of that time lag

Process & Methodology

- do we have a formal process? - are steps confirmed in the CRM? - what steps in process are they measured on? - why do so many deals get stuck in the pipeline - how many pipelines do you have? existing up/cross sell? new account? different products? - at what stage in process do most accounts drop off - why don't our people book more meetings? - why don't our people create more projects - do we compete effectively against all competitors? including industry giants? - do we know what it would take to compete against the giants? - what's teh value proposition? can all of your reps articulate it? - how many have an elevator pitch? - How do you differentiate from competitors? - What questions is your team trained to ask? - do they sell value? tell me more - do they sell consultatively? - how deep do they go? how many questions do they ask? do they understand the compelling reasons someone would buy?

Training & Coaching

- Do we train enough. when did you last have formal sales training? - which people are trainable? which resist? - what percent of their time do you managers spend coaching? - experience tells me they probably focus on pricing, quotes and technical features? is that fair? so not so much on precall planning, post call debrief, tactical sales, role playing, motivating? - how is coaching structured? - how do they decide what each rep needs specific coaching on? - do they know the real strengths and weaknesses? - who's improving? who's not? why? - what have you done to hold them accountable? - how do you measure the impact and effectiveness of coaching? training? - do you know whop's most open to coaching? would it help to know this? - do reps have territory and account management plans? how often are they reviewed? what happens if they're falling behind? - are the plans meaningful roadmaps? - do your managers know what motivates each rep and how motivated they are?


  • Do we pay enough?
  • Are you paying reps not to work?
  • Are our incentives driving results?
  • How can we understand what incentives will motivate which people?
  • How is compensation structured?

Target Accounts

  • Do we have a properly identified list of target accounts?
  • Do we have clearly defined expectations for our reps' activity in those accounts?
  • Do marketing and sales collaborate on target account outreach?

New Logos

  • Why does so much of our sales come from existing accounts?
  • Do we have the right expectations for prospecting and new account projects?
  • What's a new account worth/year?
  • How many do we need to hit growth targets?
  • What happens if you don't hit targets?
  • How many does each rep need to hit their target?


  • Why is our forecast often so innacurate?
  • Why do so many deals end in no decision?
  • What complications do inaccurate forecasts cause in production and planning?


  • What marketing and sales metrics should we track?
  • Can we track all the KPIs we want to? If not, why?
  • How often are KPIs reported? Are they public within the company?
  • What's our closed/won rate?
  • How long is our sell cycle?
  • What percent of business is new logo business vs. repeat?
  • What's our market share? How much have we gained annually for the last five years?
  • If we haven't gained significantly, do we know why not?
  • What are our costs & roi? cost/lead, cost/sales meeting, cost/opportunity, cost of customer acquisition, average deal size/margin/net, lifetime value/customer (reorders, spareparts, etc.)


  • What CRM should we use?
  • Is it correctly configured?
  • Why don't our sales people use CRM?
  • Are sales pipelines clearly outlined according to our process? 
  • Is opportunity qualification built in?
  • What do prospects and customers have to do to reach us? Can they text? Chat? Call?