I have learned that one of the hardest parts of leadership within a high-growth company is being honest. Honest about deadlines, budgets, team performance, and level setting with customers and investors on expectations.

Things fall apart when you start to give on honesty. When you fail to address a teammate’s poor performance, it directly hurts both them and the company. When you fail to clearly set expectations and be honest with the entire team about whether or not we’re meeting the mark, opportunities are lost, outages happen, and trust is lost. And when you fail to be honest with your customers - especially when something they’re demanding is harmful to your business, you may placate them in the short run but you hurt your stakeholders, and potentially the customer later on.

One of the most important lessons I have learned over the past few years is that honesty delivered with tact and grace trumps all. Never be a coward. Always be honest - no matter how badly it hurts, or how severe you think the reaction will be. Even if you may lose the deal, or someone may lose/quit their job as a result of that honesty.

If a relationship is lost over tactfully delivered and graceful honesty - good. You probably didn’t want that relationship.

If a deal is lost over tactfully delivered and graceful honesty - good. That prospect probably wouldn’t have been a good client or partner.

If an employee quits over tactfully delivered and graceful honesty - good. You probably didn’t want that person on your team.

If you are too much of a coward to deliver tactful and graceful honesty when the time calls for it - find a role where it isn’t required of you. Find an individual contributor role or a role that does not involve confrontation. Find a role where you’re not managing a team or customer relationships. People depend on you to be honest whether they realize it or not.

If you want to be a leader of others, you must first be a servant. If you want to foster trusted advisor relationships, you must first be a servant. A servant must be brave enough to tell the truth. Why? Because the truth sets boundaries. The truth protects both you and them.

I have to remind myself this everytime I have to have a hard conversation. But I have found honesty to be a muscle that can be exercised. If you practice it long enough, delivering tactful, graceful honesty can become muscle memory.

Trusted advisors and leaders tell the truth - especially when it’s hard. Always when it is hard.

Proverbs 24:10: If you falter in a time of trouble, how small is your strength!