In the dynamic professional landscape of Boston, the journey to achieving peak employee performance is an ongoing pursuit. A Gallup poll found that employees would rather receive negative feedback on their performance than no feedback at all. However, the terrain of delivering constructive criticism can be fraught with pitfalls. Even seasoned leaders like Carter Cast, who ascended to the role of CEO at Walmart and now imparts wisdom as a professor at Northwestern University’s Kellogg School of Management, can vividly recall a scathing performance review early in his career. He was labeled “unpromotable” due to his perceived “obstinacy” and “insubordination.”
“In retrospect, that critical feedback was the best gift I ever received,” he wrote many years later in Society for Human Resource Management magazine. “It caused me not only to be more self-reflective about my own behavior, but to find out why talented people derail.” He recommends a straightforward approach: offer regular, honest feedback and avoid succumbing to a prevailing cultural trend that places excessive emphasis on strengths, even when there are glaring weaknesses. Balancing this delicate act is a challenge for any supervisor.
Built In Boston was able to explore this topic with accomplished leaders at Forward Financing, Rue Gilt Groupe and Stavvy. Each manages to navigate that balance, staying true to their organizations while also empowering their employees to evade setbacks.
Forward Financing is a fintech company that provides fast, flexible capital to underserved small businesses.
Give us a sense of your experience with helping direct reports turn performance around. Describe your approach to the topic. What role does empathy play?
I’ve enjoyed working with teams at all moments of my life. A common theme of my experience has been leading teams from an early stage—when they’re still figuring out who they are—in terms of operations and helping them identify a direction, structure and goals. In some cases, you face a team with outstanding credentials that cannot find a common purpose, or a group that can’t figure out the required tools to solve their most pressing challenges. In all cases, the pivotal moment comes from a combination of empowerment, commitment, accountability and care. Yes, care. Caring about people as human beings, creating connections and earning trust demands a different level of involvement from a leader, and can be transformational for a team.
What advice do you have for newer managers who aren't sure how to tackle the topic of performance with their direct reports?
Empathy is not easy, yet it is very rewarding. Being able to listen and come to a conversation without judgment requires your full attention. The purpose of these conversations is not necessarily to find the source of the waning performance, but to find the disconnect between the individual’s purpose and the aspirations of the organization. Once you identify the disconnect, you then need to find a path forward for the individual, build a bridge and create goals to re-energize and engage them.
Empathy is not easy, yet it is very rewarding. Being able to listen and come to a conversation without judgment requires your full attention.”
In my experience, a crucial pillar of best-in-class performance comes out of a recognition of common ground between a leader and an individual. Finding that common ground is what you should pursue as a leader to foster engagement and commitment.
How can newer managers build their empathy muscles to better handle the challenges of these conversations?
I have several ways to handle challenging conversations. First, do not procrastinate. A timely reaction is key; things will not be solved by themselves and something with an easy fix could get worse. Additionally, approach the conversation with a candid and positive intention. Be firm on your expectations and offer help; you must mean it. Roll up your sleeves, become the number one fan of that individual and assist them in reaching their optimal performance level.
It’s also crucial to ask open and enabling questions. Share context, gather the other person’s insights and share your personal experiences. Recognize and acknowledge fears – fear of change, fear of success, fear of speaking up. Identify what fears may be standing in the way of performance. Lastly, set clear expectations on next steps and what deliverables should look like; make sure there is a definition for success.
It's not necessarily about being liked— but if that is an outcome, even better! It’s about being recognized for your assertive style, for your sense of fairness and honesty, for following through on commitments, for speaking clearly, for listening attentively, for challenging the status quo respectfully and again, care. Care about that person and approach them with mindful awareness.
Give us a sense of your experience with helping direct reports turn performance around. Describe your approach to the topic. What role does empathy play?
When I notice a member of my team is struggling, I always schedule some time to meet with them individually. I want to let them know what I’m seeing and hold a safe space where they can feel comfortable sharing with me what’s going on. Just knowing that they have a manager who’s noticed something different and giving them the one-on-one time to be heard is incredibly powerful.
I’ve found being clear and firm on expectations while remaining kind and present has been successful in turning performance around.”
If there’s a problem outside of work that’s causing a distraction, you can work with the direct report to strategize a workaround. If not, this is a great way to reset expectations on the role and/or project that the employee is falling short on—and make sure you’re aligned on priorities. I’ve found being clear and firm on expectations while remaining kind and present has been successful in turning performance around.
I’m fortunate that the values at Rue Gilt Group that resonate most with me—’Kind, Empowered and Collaborative’—align to my empathetic leadership style. As a leader, it makes my job a little easier when the tone and support from the top is aligned and there’s a common understanding across the organization.
What advice do you have for newer managers who aren't sure how to tackle the topic of performance with their direct reports?
Performance concerns should be addressed in a timely manner. That said, if there's a fundamental misalignment of skills and expectations it's important to address them in a meaningful way with the goal to, as we say, "manage up, not out.”
When identifying the root cause for the performance concern, consider whether the issue is a lack of skills that could be improved with training, a result of a miscommunication/misalignment of expectations or the person's skill set or aptitude is just not a match for the role.
As you're preparing feedback, consult with your network—both inside and outside of your current organization—for advice if you're feeling stuck or confused. I can't stress how invaluable it has been to have sounding boards and a support system when preparing for difficult conversations. I also suggest talking with your direct manager for tips and leaning on your HR business partner for coaching on the process and/or how best to frame your feedback. If you've addressed the root cause and are still not seeing positive changes, your HR business partner can help guide you on how to proceed.
How can newer managers build their empathy muscles to better handle the challenges of these conversations?
One of my favorite books that I read early on in my leadership journey is “Start with Why,” by Simon Sinek. I highly recommend all new managers and leaders to get a copy and read it. The concept is so basic—ask questions to understand. When we ask questions, we’re saying that we want to learn more. It’s about being vulnerable, letting our guard down and creating opportunities to share experiences and learn from each other.
Simply stepping back and putting yourself in your direct report’s shoes really helps to put things into perspective. Thinking back on your own professional journey, who had the greatest impact on you and why? How would that person approach a situation you’re dealing with? That simple pause and reflection has helped me approach situations that are challenging and ultimately create a team atmosphere that’s supportive and kind.
Maya Angelou said it best. “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
Give us a sense of your experience with helping direct reports turn performance around. Describe your approach to the topic. What role does empathy play?
Managing performance is an integral role that people managers play in supporting and developing their team. Luckily, in my role at Stavvy, I have the opportunity to partner closely with many of our people managers. Understanding what’s motivating your team can help get team members back on track.
As a manager, it’s your responsibility to connect the team's tasks back to your department's functional goals. It’s equally as important to be clear about outlining the performance expectations of one’s role in order to convey where any current gaps may exist. If you can get specific in these two areas, you can derive a sense of individual purpose for them in articulating what competencies or behaviors need improvement and why.
In all cases, leading with empathy in an effort to assess the root cause and foster receptivity to feedback will be key. Asking the right questions and employing active listening techniques can foster a safe and open environment where you can meet others where they are and craft a plan that mutually supports the best path forward.
What advice do you have for newer managers who aren't sure how to tackle the topic of performance with their direct reports?
It’s important to set the stage by investing time in coaching and development conversations early on. Carving out the space to meet with your team members individually on a routine basis and giving them your undivided attention goes a long way. Start by asking questions to get to know them better. What are their strengths? What tasks do they find themselves losing track of time on? Where are they being challenged? Creating a successful foundation for delivering feedback stems from a relationship built on trust and mutual understanding.
Carving out the space to meet with your team members individually on a routine basis and giving them your undivided attention goes a long way.”
By taking the time to get to know your direct reports, you demonstrate to them that you care about their growth and long-term success with the organization. This allows difficult conversations to gradually become easier as there will be common ground in recognizing you have their best interest in mind. Focus on providing frequent, informal feedback that addresses specific behaviors versus personality or personal preferences. Also, keep in mind that feedback goes both ways. As a manager, you should ask for feedback regularly to ensure you’re supporting your team to the best of your ability, such as adapting your approach to different learning styles.
How can newer managers build their empathy muscles to better handle the challenges of these conversations?
At Stavvy, we trust and assume good intent. This connects back to our company value, ‘The Fearless,’ where we believe we are better because of our differences, successes and failures.
We are empowered to actively participate and speak openly. We are disciplined to respectfully listen and react without hesitation. This mindset fundamentally drives the way we think about our working relationships and interactions with fellow Stavviators.
When you assume good intent and come from a place of curiosity, you can discern how to redirect certain behaviors to better match their intended outcome by gathering critical pieces of information to understand the situation. When you take this approach, you will be less likely to generate feelings of defensiveness. This also enables someone to reflect in real time, potentially coming up with their own solutions or encouraging collaborative problem solving. Keep in mind that your emotional state will set the tone for these conversations. Be mindful—you want to ensure you’re creating a safe space for open and honest dialogue.
