# Interviewing a salesperson for an MSP **Author:** Gaidar Magdanurov | **Published:** 2026-10-19 **Tags:** Business **Summary:** Hiring good people is hard. But when you have good people, they do the work for you, and you learn from them. --- "How do I hire a good salesperson for my MSP?" is one of the top questions MSP ask influencers, advisers, vendors, friends, and family. Sales candidates can describe a successful career, join the company, and barely sell anything. Or, even worse, close deals on promises, unclear scope, and leave the technicians managing expectations the price never covered. Most MSPs were there... Sadly, there is no silver bullet in finding a perfect salesperson, yet there are a few things that can increase the chances of success. ## Define the job well Decide whether you need someone to generate new opportunities, close qualified inquiries, expand existing accounts, or build the sales process itself. A limited number of candidates can cover all responsibilities. Focus on what is most important for your business. Write down the profile of customers you want, the services you expect to sell, where opportunities come from, and what technical support the salesperson will receive. Clarify who owns pricing, proposals, and contract changes. Show candidates the role as it will operate. If the owner supplies introductions and joins every closing conversation today, do not assume a new salesperson will immediately reproduce those results alone. The results you have now include you. During the interview, you should test the work you plan to transfer to the salesperson, and it should show what support the person can expect. Clearly define how sales performance will be measured. A quota can measure annual contract value, new monthly recurring revenue, and one-time project revenue. Discuss the candidate’s views on the quota design and how it incentivizes their behavior. ## "Automate" the search Prepare the core questions and scoring criteria before you meet candidates. Use them with every candidate, evaluating them on the same criteria. It will save time and simplify the decision process when you need to compare multiple candidates. Build an agenda template that works for you. For instance, a 30-minute initial interview and a 60-minute follow-up interview. Include 5–10 questions about past experience. 3-5 exercises for pitching, objection handling, and follow-up. Fit the agenda into the time slot and follow through. You have a standard operating procedure for technical issues - have a procedure for the interviews. ## Focus on practical experience Ask about a deal the candidate won. Ask how the opportunity originated, what the buyer needed, what the candidate personally did during the sales process, and what happened after handoff to delivery. The win shows you the steps they take. Then ask about a loss. The loss shows you whether they noticed the evidence they missed, and what were the learnings from the loss. Some ideas for the questions: - Walk me through a deal you generated yourself. What changed between the first conversation and the signed agreement? - Describe a deal you expected to win and lost. What evidence did you miss, and what did you change afterward? - Tell me about a promise you refused to make to a prospect. How did you explain it? - What feedback changed how you ran opportunity discovery? Give me an example of the next call where you used it. - How did your previous company measure quota, and how much of your result came from new customers, renewals, and expansion of existing accounts? Ask follow-up questions until you understand the candidate's contribution. Focus on practical experience; don't let generic answers distract you. ## Test in a discovery call Ask the candidate to do a simulated opportunity discovery call with you. Give the candidate a short service sheet. Provide enough information that the exercise does not turn into a test of your unpublished product knowledge. Then role-play, serving as a customer. Watch whether the candidate focuses on the customer problem or on your offering. Discovering the problem and proposing a solution is a good sign. Focusing on the offering, not asking the customer enough questions to identify the pain, is a bad sign. Introduce some trick questions, such as asking for unlimited on-site support at no additional cost, and see how the candidate will reject the request. It is a bad sign from the start if they agree and then pass on a contract that will not be profitable for your MSP. ## Give feedback After you get your questions answered and observe the behavior in the exercise, provide feedback - your observations on what could be improved and why - and watch the reaction closely. Look for the understanding of the feedback and reaction to the feedback. The business evolves; salespeople shall be able to develop and evolve as well. See how they treat the feedback and if they are coachable. If the candidate challenges the feedback with solid arguments - it is a good sign that they will not just say "yes" to everything you say, will have their own opinion, and won't hesitate to share their observations. ## Scorecard example Use a simple scorecard tied to the job description you created to evaluate candidates. Here is an example you can use as a start. Criteria 1: concern 3: adequate 5: strong Discovery Pitches before understanding the problem Establishes the problem and its impact Tests assumptions and prioritizes the problem with the buyer Buying process Assumes the contact can decide Identifies decision authority and timing Establishes decision steps, constraints, and a useful next action Commercial judgment Promises unsupported scope or discounts Explains scope and checks exceptions Connects scope, delivery effort, and buyer value without inventing commitments Learning Not listening to the feedback Accepts the feedback, suggests adjustments Listens to the feedback, internalizes it and comes back with suggestions Follow-up Misstates facts or omits agreed actions Produces an accurate summary and next step Separates commitments, open questions, and owners clearly ## Check references Ask the candidate for references, and have quick calls with the references to address any of the concern areas. Make the calls short, friendly, and focused on the specific examples. One important note: if you got to this stage and you have doubts that the candidate actually did what they pitched to you— don't waste your time calling the references and checking if that was the truth. If you have doubts from the interview, move on to the next candidate. Hiring good people is hard. But when you have good people, they do the work for you, and you learn from them.