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7 More Questions on Leadership with Joseph Messina

Name: Joseph Messina

Title: Managing Director, HR Effectiveness

Organisation: ChenMed

Joseph has over 18 years of HR and Talent Acquisition experience in the Healthcare and Investment Banking sectors. He is currently the Managing Director of HR Strategy & Effectiveness for ChenMed in Miami, FL.

Joseph’s role is to ensure operational excellence and the strategic measurement of people, process, and tools as well as ongoing business critical HR infrastructure and governance. Joseph is an SME in multiple disciplines including strategic workforce planning, budgeting and forecasting, process optimization and improvement, operational efficiency, training & onboarding, and Talent Data, Analytics & Insights. He has spoken at events such as LinkedIn TalentConnect, Syncota Talent Branding/Employee Engagement, Findly Talent Leadership roundtable, BWG Talent Leadership Roundtable, St. Bonaventure “What a Recruiter Looks For” keynote, and sits on the advisory board of TALK South Florida, Purdue University Global (MA Program), and CareerArc Innovation Advisory Council. He was also was named Top 10 Talent Professional by OnCon "Talent Icon" Award (2023) and was in the March 2023 Mirror Review cover & article, called “The Top 10 Robust Healthcare Leaders."

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

We’ve gone through the interviews and asked the best of the best to come back and answer 7 MORE Questions on Leadership.

I hope Joseph's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. As a leader, how do you build trust with employees, customers and other stakeholders?

I believe trust is earned through consistency and communication. I realize there’s many different lens to look through but if I boil it down to 3 key principles I try to live by:

1. Transparency – Be open and honest with any interaction you have with anybody you come in contact with. Look for opportunities to build credibility, share information, communicate goals and partner with them in decision making. Look for ways you can prove that you trust your employees, remove ambiguity, and show that you value open dialogue. Help others by understanding what goes into a decision (the rationale behind it) which allows you to foster a sense of inclusion and trust in that decision making process. Actively encourage feedback and seek input.

2. Empathy – Take the time to listen and focus on the needs of others, acknowledge different perspectives, always provide support when needed. It’s very hard to set aside your own bias but it’s the only way to truly connect with others. This also then allows you to create a space where honest communication and a foundation of support if felt between you and whomever you are engaging with. I believe this also will help you, as a leader, address needs of people, leading to stronger relationships and increased engagement

3. Accountability – This is something I’ve learned over time which is live by example and hold yourself accountable. Following through, consistent delivery, accept mistakes and learn from them, and always see tasks, assignments, and deliverables through. My role modeling what you expect (inspect what you expect) you can inspire others to the same, fostering an environment based on trust.

2. What do 'VISION' and 'MISSION' mean to you? And what does it actually look like to use them in real-world business?

Many people equate “Vision” to the business which it does represent a forward-looking statement that describes the future state of an organization, however, to apply it to me personally I believe it does (and should) also represent the leader’s aspirations and provide the “guiding light”, a sense of purpose and a clear direction. A clear vision, both from the org and leader, can inspire and motivate employees, guide actions, and ensure key decision making as well as strategic alignment. On the other side, a “Mission” can serve to describe the “purpose” of the organization. I try to look for opportunities to align not only myself but my team with the vision and mission and connect with the core values of the org.

Off the top of my head, how I or any leader can live the vision and mission and apply it to everyday:

1. Connect people to the Vision/Mission and consistently communicate it.

2. Setting strategic goals for the team in lock step with the organizations vision, mission, and strategic goals. Aligning individual and team goals with the future in mind allows all to row in the same directly to ultimately achieve what the organization set out to do.

3. Use the vision and mission to make key decisions. This allows you to consistently build trust and keep oneself grounded for the greater good.

4. Inspire and motivate your team (or anybody you come in contact with.) This creates a sense of purpose, engagement and meaning to your team or employees alike. The idea is to look for opportunities where you can foster commitment to the organization’s goals.

5. Lead by example. Be a role model (brand ambassador), inspire others every day through your own actions and model the behaviors or values that connect to the vision, mission for core values of the organization. If you don’t “live” it every day, how do you expect to influence it amongst your team or anybody you come in contact with?

3. How can a leader empower the people they're leading?

Empowering is not simply delegating work to others to make them feel good but rather helping your team to reach their potential. I believe that in order to unlock that potential, you have to inspire them to believe in their own skills. I believe in providing guidance but also autonomy, encouraging your team to take initiative, make (or be part of) critical decisions, and contribute by utilizing their talents (all while expanding their scope and learning new ones.) As a leader, it’s important to look for ways to increase the confidence of team, push innovation, celebrate shared successes, and provide feedback (and allow for feedback to be given to you)

4. Who are some of the coaches or mentors in your life who have had a positive influence on your leadership? Can you please tell a meaningful story about one of them?

I believe that mentors can be of personal nature or professional, every interaction can be an opportunity to learn, be mentored (or mentor), coach (or be coached) so if you don’t mind, I’ll do one personal and one professional.

On the personal side, I’ve always looked up to my father (and mother). Outside of having very big shoes to fill, he always looked for opportunities to teach me life lessons no matter how big (or small), that I half understood at the time or just sitting back and watching how he strategically viewed certain issues whether in personal life or professionally. That strategic mind, solution focused approach was something I witnessed and built into my thought process. If I do X, how does Y get impacted, should I go from A-B-C to D or go straight from A-D, if this occurs, what are the possible outcomes or ramifications of said decision, etc. He would purposely verbalize his thought process so I learn how to think things thru, painting that vision, the why and even challenged me on solutions. So outside of being the legacy of somebody with so much vision, a strong work ethic, ability to build trust and know when to push vs when to teach, it went a long way to who I am today. I have way too many memories or life lessons but if thinking about how I was shaped as a leader, whenever he could, he would introduce me to the Executives of his organization and expose me very early on. Partway I’m sure cause he was proud of me but also to expose me early on to like-minded, and like thinking people to himself. Whether it was me at a craps table in Puerto Rico (him allowing me to roll once and ruining his hot streak in front of his peers, the executive leadership team), to sitting me in his office and inviting in other executives to have conversations with me, to teach me, or just so I can watch, gain confidence, and understand how to engage and understand/shape how I speak when engaging and knowing my audience is important. I also believe that exposure also showed me how he was able to garner respect, as I watched CEOs, CFOs, CHROs all hold him in such high regard and asked for his opinion more than most others. I’m not saying I was in important meetings obviously but the command of his subject matter, how others confided in him, how he was able to speak to his audience (especially impressive was despite “rank”, as an Executive, how he treated and engaged everybody, regardless of title.) Through it all, and I’m sure he mentored many, including me, but for his whole career he would seek feedback, remained humble, and always looked for opportunities to learn himself. On the inverse to him, albeit this is a career focused answer, I have to also give credit to my mother, who selflessly raised my sister and I, she helped me understand love, empathy, support and encouragement, values and morals, education and curiosity, sacrifice and selflessness, positive reinforcement, and relentless love and devotion. Again, the characteristics that I feel embody a leader, and something that I try to exemplify.

I can only hope by the end of my career, I can have the successes my father had in his career, impacted my own family (leveraging both my mom and dads characteristics) and others lives and be held in the same regard as he is in career. They are both now able to able to continue to mentor me but also be able to see their legacy continue through me and both their many teachings. I just hope I can continue to make both proud and carry on that legacy for the next generation.

Professional: Very early in my career, I had a leader who the only time we engaged was when they needed something from me. I was told that my job was to give the information and then move along to the next time I’m needed, they will handle the “face time” with whomever they are presenting too. Not the greatest early on experience for me, especially transitioning from my father, the mentor, to this but it would cause me to questions my confidence and blame myself for perhaps being too young and inexperienced. I had blamed myself as just “not being ready” or “they probably didn’t want to hear from me anyway” but reflecting back now almost 20 years, I realized it was actually a flaw of that manager rather than a flaw of mine. Partway thru my tenure at Company X, I received a new leader, one of the first actions was to sit me down, get to know me, empowered me, uplifted me, explained the why, painted the vision and allowed me the autonomy to not just run the information but encouraged me on how to paint a story, articulate and allowed me the rope to present to the leadership team on multiple occasions. I wasn’t always perfect, but this leader would have open dialogue, constant communication and open feedback each time – so I continued to gain in confidence, honed in my presentation ability and learned. Being more specific, albeit early in career, and it was profound to watch, this very tenured leader, in a meeting, had been asked a question that they couldn’t answer. Instead of trying to make something up, they said “I’m not sure.” It was a lesson in humility and being okay with not knowing something. However, in the moment, I started to sweat a little bit cause I actually knew the answer myself, with self doubt creeping in, this leader did something that changed my mind-set, he called on me, in front of everybody, and trusted that I would articulate the answer. Not only did he trust me in that moment, when I hadn’t experienced that in the past, he was humble enough to give me the spotlight at risk of his own getting “showed up.” Afterwards, he smiled at me, patted me on the back, encouraged me, boosted my confidence and continued to mentor and give me tasks of increasing responsibility, even if that meant outside of my comfort zone cause he believed in me and saw my potential. To this day I have taken many of these characteristics that made me who I am today. It also helped me realize what kind of leader I wanted to be (and didn’t want to be.)

5. Leadership is often more about what you DON'T do. How do you maintain focus in your role?

One major key to my outlook is prioritizing, dedicating time to priorities and trying not to get blinded by anything that would take off the course towards the ultimate goal or that doesn’t help step me/us closer to the vision and mission of the organization (and desired outcome.) This could be things like setting boundaries, practicing time management, and staying disciplined. My natural inclination is to “go off track” and “try to do it all” but reminding myself to redirect that energy and my attention, blocking time slots, breaking down tasks in the “easy to digest” bites, and being honest about communicating preferences, like time blocks or general availability to ensure I can remain focused, restrict potential distractions or interruptions. Not only is it important to do this for my own sanity but also to live by example and promote the same from my team. As a leader, I try to stay cognizant in allowing the same for my team members and protect them as well. Lastly, I focus on outcomes which also helps me stay focused and prioritized. I try to visualize the bigger picture and avoid getting lost in the little things that can sidetrack. I also practice delegation of more tactical items, which allows me to stay more strategic and focus better.

6. If you fail to plan, you plan to fail. Everyone plans differently. How do you plan for the week, month and years ahead in your role?

This is a really interesting question that can be answered in a few ways so instead of providing a plan outline, my mind is going to the thought process behind planning, so I hope you don’t mind that lens here. If I think about “how do I keep myself on track and future thinking”, there’s 3 “critical” items I try to stay on top of. First, I try to set clear and achievable goals and objectives for myself, both short and long term. Each objective should be a building block to whatever outcome I am expecting. I tend to “work backwards”, I envision what it looks like years ahead and try to backdate key milestones to that anchor as I plan. However, as visual as I am, if I don’t present clear goals and provide myself a sense of direction, something to focus on and a guiding light for decision making or resource allocation I have a more difficult time staying out of the weeds and not focused on the “now” only, losing sight of the now and how it impacts the future. Secondly, I try to prioritize work strategically. Base priorities on impact or importance. If priority X doesn’t help us step up a rung towards the organization goal, I may deprioritize it. Resources are a precious commodity, so I try to focus myself and my team on the items that can deliver the biggest impact and focus on high value objectives, maintaining maximum productivity. Lastly, I am constantly planning and re-adjusting. Plans changes, strategies change, alignment and focus changes, so I try to review and re-set on a regular cadence Being a data first mind, I looks for key indicators to gauge performance/productivity, identify gaps which allows me to adjust quickly with reasonably high probability of making the “right decision, at the right time.” I realize there’s many other ways and more variables than what I expressed here but I think this would be a solid foundation and help you and your organization be successful in the short, mid and long term.

7. What advice would you give to a young leader who is struggling to delegate effectively?

Learn to let go! Look for delegation opportunities, and once you do delegate allow your team the autonomy to complete it in their own way, learn from mistakes (if you stay close you can head this off). It’s imperative that you trust your team to ensure that they will deliver the results.

Trust your team. Recognize that you have and more than likely hired a talented and very capable group of people that are capable of handling the task at hand. Trust their abilities and give them the opportunity to excel.

Define clear expectations. Clearly communicate your expectations, desired outcome(s) and objectives as well as key deadlines for such. It is on you, as a leader, to provide all the necessary information and to set up your team for success.

Strength Matching. Understand the skills of your team and well as their strengths and weaknesses. Delegate tasks not only that match their skill set (but also their abilities and interest.)

Support and Guide (Don’t micromanage) – just cause you delegate something, doesn’t mean you don’t support and provide guidance, recommendations, are available to answer questions, bounce ideas, provide clarity or just offer feedback. A lot of young managers either can’t let go or let go but micromanage. Find that balance.

Open the Communication Channels. This can be feedback sessions, your team feels comfortable with asking questions or for help, can collaborate when needed and allow for mutual feedback. Conduct regular check-ins on progress, milestones, bottlenecks, and the outcomes of said tasks.

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