Dustin Stewart

If you want to know something then you have to ask! There are five mechanisms that I typically employ if I want this type of information in a team/company: 1. Direct feedback via One on Ones. Ask directly about work/life balance. 2. Encourage skip level meetings where employees may find it easier to speak truthfully. 3. Periodic surveys (optionally anonymous). 4. Infer positive results by higher retention rates and tenue. 5. Conduct exit interviews, as employees are most likely to be candid as they are leaving.

Know your audience and cater to their preferences. In most cases it will be important to keep emotions in check unless you feel it strategically helps the conversation. You have to help the boss to see how the concerns you are bringing are concerns that should be shared as it is much easier to bring about necessary change. Paint a picture of possible solutions and be sure to tie that to how it will ultimately solve problems or reduce noise or friction for the boss. "Help me, help you!"

People are unlikely to solve a problem they don't know exists, so it is important to start by ensuring that the team member knows that their behavior is both noticeable and having a negative impact on the team. Ensure they understand that you're having the conversation because you care about the outcome; most people would avoid hard conversations at all cost and to everyone's detriment. Ensure it is truly a conversation and listen for any feedback the team member may have that can help you coach them or set them up to succeed (ex. adjusting their shift by 15 minutes). Finally, agree to or reaffirm what "good" looks like and set a time to follow up to check progress, ultimately resorting to disciplinary action if progress isn't made.

"It is lonely at the top" The thing that has helped me the most is trying to make that statement above as inaccurate as possible. For me, it's important to surround myself with people on a similar path who can relate to my situation and either offer real advice or just empathize. This can happen naturally as you make connections, but it may also be worthwhile to pursue peer groups or professional groups. Having a mentor can make a huge difference, as well-- even though most mentors won't ever refer to themselves as being a mentor. Just keep an eye out for people that have made it further up the mountain or have already made a few trips. :)

You have to develop trust as a foundation, which is something Patrick Lencioni explores in his book "The Five Dysfunctions of a Team". It helps if you're leading a small team of people you know, but if you aren't then you'll have to build trust capital from nothing. This usually means being transparent before expecting transparency, proving out your humility and commitment to personal and shared goals, and the ability to be both honest and caring. It is about openness, candor, commitment, accountability, and collective success.

Especially with new employees, I start by letting them know that I give them feedback BECAUSE I care for them-- not because I don't! It is more rare that employees will have someone willing to invest in them by helping them see other and better ways of doing things. If it's proving exceptionally difficult then I try to relate the process of giving/receiving feedback to a hobby of the employee's as almost everyone can relate to the process of being coached to improve at basketball, sailing, painting, etc. It is easier to keep silent, but good leaders want to share what we've learned with the people we're developing.