Ask Amanda is a new advice column for you to anonymously submit questions about the soft skills and hard topics you need to master as a go-to-market leader.
My boss was an early employee, and we’re not growing rapidly. Sometimes, he doesn’t know what he doesn’t know, and I don’t want to fracture our working relationship by hurting his ego. Advice on how to deal? Also, our investors keep asking for feedback on him. What should I say?
Signed, Pavilion Member
The reasons that the company is not growing rapidly could run the gamut: poor product market fit, competitive landscapes, product delivery issues, brand awareness, market conditions, poor operational excellence, lack of talent, go-to-market strategy, and more. (Sometimes, companies can’t get out of their own way.)
Putting all this on your boss might be unrealistic in terms of expectations. So what can you do? You can actively participate in helping your boss and the company grow. One way would be to engage with your boss by asking questions and discussing his answers.
Once, a friend asked me: “Are you open to feedback?” Asking this question might be worth a try. However, brace yourself because many people will say they are open, listen to the feedback, and then have all kinds of emotions about it - in short, they really aren’t open to feedback. The way to approach this question is with tenderness, thoughtfulness, and care. If you can’t bring that to the table, try another approach.
A therapist once suggested a magic question to me: “What’s your plan?” followed by, “Have you thought about X?” Asking your boss these questions allows him to take ownership without you having to do it for him. Staying present to hear the answers and engage in the dialogue is a way to show your support. This dialogue opens the door to sharing your personal perspectives on the growth challenges. It also affords you the opportunity to learn about factors you may not be aware of (humility) and discuss ways to drive the company forward with your boss. Leveraging the problem analysis and critical thinking skills you both bring will only be a benefit, as the more brains on a problem, the stronger the solution. Further, you open the door to align with and improve your relationship with your boss, not fracture it - thereby growing your interpersonal skills.
As for the investors, be honest. Growing companies is hard. No single individual has all the answers - and it is unfair to assume that to be the case. Once you’ve engaged in dialogue with your boss, sharing your perspective on the situation with investors will be easier, and you won’t feel like you are going behind his back, proving your trustworthiness. Shoot straight, and your integrity will lead you through no matter what.
Amanda regrets she cannot reply to questions individually. By submitting your questions to Ask Amanda, you agree to have them published anonymously on Pavilion’s Blog.
Amanda developed her business acumen by repeatedly scaling metrics and creating value for a number of VC-backed startups (YouEarnedIt, BlackLocus, Infochimps), and established technology companies like: Rackspace, Dell, SolarWinds (Forbes #1 Best Small Company in America), NetQoS (bought by CA), PeopleAdmin (a Vista Equity Portfolio Co), and Pervasive Software. She is a longtime startup mentor at Capital Factory and Tech Stars Austin. Amanda is an accomplished speaker, board member, and advisor who believes in integrity, the value of community, and the power of connection. She has lived and volunteered in Austin for nearly 30 years.