Ecclesiastes 5:9 says, “After all, a king who cultivates the field is an advantage to the land.” I grew up in software sales of the 90’s…a time where the boss was used only for closing events or executive face-offs. This has purported a sense of laziness within today’s sales brass, but the best sellers look for creative ways to defy this culture and engage them in a productive manner. I’ve managed sellers as well as managers, and the best reps follow a few best practices when it comes to engaging leadership.
- Have a specific objective. Your boss most likely does a few things well…and a few things not so well. Understand what those are and be up front about it. I, as example, am good at asking some of the tougher or more sensitive questions as it relates to things like, budget, buying authority, path to funding, etc. My best reps recognize this and outline a specific event that allows me to build rapport with the buyer and go in for the kill.
- Be assertive. It’s endearing to see a rep gather a group of people on an internal call, outline a call plan, and specifically identify next steps along with stakeholder roles. Whether or not I agree, I’m more inclined to engage if my rep is assertive with the ask.
- Outline a persona map. Being a quarterback on a deal means you have to know all personalities both internal and external…AND know how to match them up properly to obtain the best outcome. If your boss is an alpha-male, matching him up with a CFO who’s a female introvert could spell disaster. Be specific with your boss and tell him who to build a relationship with and why.
- Outline your boss’s engagement based on the overall strategy within the account. It wouldn’t be out of the norm to have my rep engage me knowing the role I’d play could get me knocked off the chess board. Sometimes you need a provocateur, and this can often backfire. If it does, your boss is expendable…you on the other hand, are not! Tactical example might be, using your boss to send a note to a CIO when we’re too low in an account.
- Map your boss’s personal win to the engagement. Many sales leaders don’t get a lot of recognition but crave it. Some could care less about a pat on the back and want the next promotion. It’s important to know what drives them and use your engagement model to appeal to it. Good example is, I once had a boss who was recognition-driven…so I gave him the task of engaging our SVP of Engineering on customer meeting that was needed in an important evaluation step. I could easily have engaged the executive, but this task was best given to my boss at the time as he liked to be seen and known within the C-suite of our company.
Managing up doesn’t have to be as hard as it sounds. Do it well and you’ll get the king off the terrace and help you till the land for your advantage!
Software Sales Blog 