Strong organizations recognize that leadership disconnected from daily operations quickly loses touch with reality. This article outlines practical methods for maintaining meaningful connections between executives and frontline teams, drawing on insights from leaders who have successfully closed this gap. The following practices help ensure decisions are informed by the people closest to customers and the actual work being done.
- Ask What Leaders Miss
- Have Executives Do the Work
- Keep Leaders Hands-On
- Schedule Direct Employee Check-Ins
- Put Leaders in Customer Contact
- Conduct Monthly On-Ground Visits
- Answer Every Feedback Request
- Host Agenda-Free Frontline Sessions
- Lead Intentional Listening Rounds
- Maintain a Shared Operating Rhythm
- Ground Plans in Unfiltered Notes
- Foster Open Team Dialogue
- Create Direct-to-Shift Communication
- Test Decisions With Frontline Staff
- Hold Recurring Listening Hours
- Retain Direct Client Contact
- Explore Needs Behind Requests
- File Expenses Without Shortcuts
- Review Uncensored Signal Reports
- Conduct Seasonal On-Site Reviews
- Bring Frontline Insights to Discussions
- Rotate Leaders Into Client Calls
- Make Leaders Write Awards
- Require Firsthand Problem Reports
- Present Raw Employee Words
Ask What Leaders Miss
One practice that has worked well is making frontline feedback part of the leadership routine instead of waiting for it to surface through reports. We regularly bring customer-facing and operational issues into leadership discussions, especially recurring problems that employees are seeing before they show up in metrics.
The key is to ask, “What are people closest to the work seeing that we are missing?” That keeps leaders connected to real friction, gives employees a clearer voice in decisions, and helps us catch problems earlier instead of managing them only after they become bigger issues.
Alex Yeh, Founder & CEO, GMI Cloud
Have Executives Do the Work
Having a clear structure helps more than good intentions. CADRE started out planning to build software for dispute resolution and ended up running the services ourselves, on our own platform. That means the people building the product and the people doing the daily work sit inside the same system, looking at the same records. Leadership can see the friction directly instead of hearing about it through several layers of summaries.
The practice I’d back is deceptively dull: make senior people do the work occasionally, not observe it. Sitting in on a process tells you very little. Actually handling a matter end to end shows you where time is being wasted. I’ve never come away from that without changing my mind about something.
The part worth guarding is what happens to what you hear. If a frontline observation surfaces and nothing visibly changes for three months, people quickly start feeling that there’s no point in raising things, and no listening exercise recovers from that.
Rajneesh Jaswal, Co-founder, Cadre ODR
Keep Leaders Hands-On
As a leadership team, we’ve made a collective commitment to keep “getting our hands dirty” in our respective departments as a way to maintain good connections with our frontline workers. This means that I’m still creating analytics dashboards and running reports myself about 10 hours a week in addition to my leadership duties. It helps me stay familiar with the tools and workflows of my direct reports and means that I can usually anticipate potential complaints before they become crises.
Mark Sturino, VP of Data & Analytics, Good Apple
Schedule Direct Employee Check-Ins
One of the management techniques we put a lot of stock in is the power of 1:1 conversations. Everyone in a leadership position, myself included, is responsible for having at least one direct check-in with each employee under them. For team leads, we try for once a month, while the C-suite, with more duties and more people under them, manages at least one per employee per year.
Ranjith Raghunath, CEO, CX Data Labs
Put Leaders in Customer Contact
The gap usually opens because information reaches leadership already processed. By the time an issue arrives as a summary or a number on a dashboard, the texture has been stripped out of it, and the texture is where the useful part lives. A metric tells you complaints rose. It does not tell you that the same three people spent all week apologising for something we could have fixed in a day. So the aim is to keep leaders in contact with the raw version, not a tidier one.
The practice we hold to is that everyone in a leadership role spends time in actual customer contact rather than reading about it. Sitting with support, hearing the calls, reading the complaints in the customer’s own words. It is uncomfortable, which is part of the point. It also quietly changes the relationship, because the people on the front line stop being a source of reports and start being colleagues who know things you do not. What I try to avoid is turning it into a scheduled ritual that people attend and forget. The value comes from what gets changed afterwards.
Paul Sharpe, CEO, Easy Business App
Conduct Monthly On-Ground Visits
Our company follows a monthly practice under which the members of our senior leadership team get on the ground to interact with frontline employees, including on-site staff, sales professionals, and customer service representatives. This is much better than a formal presentation or meeting in the office, as it gives top management direct insights into the experiences, needs, perspectives, and challenges of frontline workers. During these on-ground sessions, they aim to understand the things that are working, those that need to be changed, the areas where frontline staff struggle, and what frustrates customers. We have an action tracker through which leadership responds to the issues that frontline employees may raise with suitable suggestions. Therefore, this practice builds greater trust between both parties, as it helps senior leadership make well-informed decisions that align with the ground realities of what frontline workers face every day.
K. Raheja Realty, GM – IT, Raheja
Answer Every Feedback Request
Keeping in touch with frontline staff should be a regular aspect of managers’ work, not something they only do when issues come up. I ask three questions during brief, frequent meetings: What’s going well? Where are you encountering needless challenges? What would you do differently if you could decide for yourself? I keep these meetings short to allow employees to be honest without taking too much time away from their work.
One rule is non-negotiable: every person who provides feedback receives a clear response. When someone brings up a concern, we either address it or provide an explanation. Before attempting to fix anything, I also make it a point to listen. When a team member reports that a procedure is slowing down client work, I first investigate what is truly going on and the source of the issue. This helps leaders make better decisions based on real situations, not assumptions.
Mollie Plotkin, Founder, Communications Expert, Mollie Plotkin Group
Host Agenda-Free Frontline Sessions
I ask leaders to spend regular time with the people closest to customers and day-to-day operations, without turning it into a formal review. This involved holding small, agenda-free frontline sessions where employees could raise friction points directly. It gave leadership better context and showed teams that feedback could actually shape decisions. It was a simple measure to encourage teamwork, bonding and trust.
Michael Gargiulo, Founder, CEO, VPN.com
Lead Intentional Listening Rounds
To keep our leadership team connected to frontline therapists and support staff at Oceanic Counselling Group, I encourage my leaders (including my husband, who’s also the CEO) to approach management the same way we approach clinical work, and that is with intentional attunement and active listening rather than reactive problem-solving. It is very easy for executive tiers to focus entirely on metrics, schedules, and operations, but emotional disconnect quickly breeds burnout among our frontline staff. As leaders, we must intentionally step into the daily realities of the staff to understand where the invisible emotional friction lies.
One specific practice I implemented is what we call intentional listening rounds. Each month, our clinic supervisors and department heads step away from administrative oversight and conduct structured, agenda-free check-ins dedicated entirely to hearing the frontline experience. Rather than reviewing case files or production targets, our leaders ask two reflective questions: Where are you feeling the most emotional or operational friction right now, and what tools do you need to feel supported in your day? This creates a safe space where staff can share raw challenges without fear of evaluation. By treating these discussions with the same confidentiality, empathy, and presence we offer our clients, leadership stays grounded in the realities of our workforce, ensuring our decisions protect the emotional health of the people carrying out our mission.
Kenza Haddock, President, Oceanic Counseling Group
Maintain a Shared Operating Rhythm
On multi-city video work, I don’t stay connected to the frontline by sitting in more meetings—I stay connected through one shared operating rhythm.
We put a single producer as the main point of contact. Every crew gets the same brief and the same technical specs. Schedule and approval changes get confirmed in writing. We check in with active locations while they’re shooting, and we review footage before small differences turn into expensive reshoots.
That practice keeps leadership wired into what’s happening in the field without making the client manage production. It also respects the people on the ground: editors, freelancers, and crew aren’t guessing which version of the plan is real.
I care about this because I came up through nearly every set role—PA, camera, grip, sound, producer. When you’ve been the person waiting on a late call sheet, you design systems that keep the frontline informed, not systems that only look clean from the office.
Tavares Beverly, Founder and CEO, Beverly Boy Productions
Ground Plans in Unfiltered Notes
A strong method has been giving leadership a standing requirement to review unfiltered frontline notes before major planning discussions. These are not polished summaries. They include raw customer feedback, recurring internal pain points, and examples of where teams had to improvise to keep delivery moving. I use that material as a grounding document so strategic conversations begin with lived experience instead of assumptions. It changes the tone of planning because leaders enter the room closer to the work.
The practical benefit is better judgment. Frontline employees feel heard without needing to escalate theatrically, and leadership makes decisions with a clearer view of execution reality, customer confidence, and the small process gaps that often grow into larger operational risk.
Sherif Koussa, CEO, Software Secured
Foster Open Team Dialogue
One practice we actively encourage at Versus Trade is open dialogue and idea-sharing within teams. I believe leaders shouldn’t have to guess what employees need, but the environment should make people comfortable enough to say it. That means regularly asking for feedback, encouraging people to challenge existing ways of working, and making space for ideas regardless of someone’s seniority. The important part is listening and, where possible, acting on what you hear.
Vitalii Bulynin, Co-Founder and CEO, Versus Trade
Create Direct-to-Shift Communication
The higher you move in an organization, the more intentionally you have to create proximity to the work. Otherwise, you risk making very informed decisions based on increasingly filtered information.
One practice we have implemented is direct-to-shift leadership communication. Rather than relying solely on information to move upward through layers of management, senior leaders spend time directly with frontline employees across shifts to share business priorities, answer questions, and hear what employees are seeing in the work.
I encourage leaders not to treat these conversations as broadcasts. The expectation is to share, ask, listen, and close the loop. One question I especially value is: “What are you seeing in the work that we may not be seeing from where we sit?”
That question matters because frontline employees are often the first to see process friction, safety concerns, customer-impacting issues, waste, and opportunities for improvement. If every piece of frontline information reaching an executive has already been filtered through several people, you are no longer hearing the frontline directly.
We also make follow-up important. When employees raise something, leaders should come back with what was done, what is being considered, or why something may not change right away. That is what turns visibility into credibility.
I do not view frontline connection as simply an employee-engagement practice. I view it as a business intelligence practice. Executive altitude provides perspective, but it can also create distance. Strong leadership requires both perspective and proximity.
JULIE CATALANO, Chief People Officer, Palmer International, Inc.
Test Decisions With Frontline Staff
I use a practice called frontline-first follow-up. When a leadership decision affects daily work, the first review happens with the employees carrying the impact, not in the leadership room. The discussion focuses on what became easier, what became harder, and what unintended consequences showed up once the decision met reality.
That sequence has made leadership more credible because it replaces assumption with verification. It also helps employees see that their experience is part of the evaluation process, not an afterthought once results are already declared. Connection grows when people recognize that leaders are willing to test decisions against lived experience and adjust before frustration becomes disengagement.
Brian Hansen, President, Rocket Pilots
Hold Recurring Listening Hours
A simple practice that keeps leadership connected with frontline employees is a recurring “frontline listening hour,” where senior leaders step away from formal meetings and speak directly with employees closest to customers, operations, and day-to-day delivery. Discussions focus on three questions: What is creating friction? What is working particularly well? What change would make the biggest difference? The critical step is closing the feedback loop by documenting recurring themes, assigning accountability, and sharing progress on agreed actions. Gallup’s workplace research consistently links employee engagement with stronger business outcomes, including productivity, profitability, and retention. Frontline employees often see operational problems long before those issues appear in executive dashboards, making direct listening a valuable source of business intelligence. Leadership teams become more grounded when employee feedback moves beyond an annual survey and becomes part of the regular operating rhythm. The goal is not simply to make employees feel heard; it is to make frontline insight part of better decision-making.
Arvind Rongala, CEO, Invensis Learning
Retain Direct Client Contact
I still run client demos. I don’t have to, and I don’t do day to day client work anymore, but half an hour in front of an actual customer tells me things no summary will. You hear where they hesitate, what they assume the product does, what they’re actually worried about.
The other practice is talking with the sales team constantly rather than reading their numbers. They’re the ones hearing objections all week. Same with support. A lot of the customization we’ve built into the platform came from the support team hearing the same request over and over and passing it up. Those features came from people answering tickets.
What leaders lose first is the texture. You keep the metrics and lose the reason behind them, and once you’re only looking at reports, you’re a step behind whoever is on the phone.
Holding onto one hands-on task, even a small one, is the cheapest way I know to stay honest about what customers are experiencing.
Lisa Bennett, Director, Sales & Marketing, DoJiggy
Explore Needs Behind Requests
The frontline in our business is customer success, because those are the people hearing what’s actually broken while an organization is in the middle of its biggest event of the year. If leadership only sees that through a summary, you end up with a list of requests instead of a list of problems.
The practice that matters most is separating the two. Someone asks for a button. A button would be a Band-Aid, and the underlying problem is still sitting there after you ship it. So the question we push on internally is what the person was trying to accomplish when they needed the button. That answer almost always lives with whoever took the call.
The other half is making it safe to raise something that isn’t yours to raise. Our team knows they can bring an idea outside their job description and go explore it. That only holds if the response is curiosity rather than a reminder of who owns what. Leaders lose frontline perspective one polite dismissal at a time.
Scott Shirley, Founder & CEO, Pledge It
File Expenses Without Shortcuts
Everyone on the leadership team files their own expenses in our own product, with no shortcuts and nobody in admin doing it for them. It sounds like a small thing. It is the most reliable way I have found to keep a leadership group honest about what the software is like to use, because you feel the friction yourself on a Sunday evening with a folder of receipts.
The second practice is that leaders take a turn sitting in on support conversations. A summary of ticket volumes tells you what is broken. Hearing somebody describe the workaround they invented months ago tells you why they stopped reporting it.
Both work for the same reason. Frontline experience does not survive being summarised. By the time it reaches a leadership meeting as a theme, the specific detail that would have changed a decision has been rounded off.
James Rowell, Chief Technology Officer, Capture Expense
Review Uncensored Signal Reports
A practice that has worked well for us is a monthly uncensored signal report built from frontline voices. We invite team members to share what slows them down, what customers are reacting to, and what leadership may be missing. Every submission can be named or anonymous, but it must describe a real pattern with clear details.
We review every report together before leadership discussions so we begin with honest feedback from the ground level. We treat the report as a starting point for action. We choose the strongest ideas and test small operational changes. Each experiment has a clear owner and a review process. Frontline employees see their insights shape better decisions and stronger trust.
Vaibhav Kakkar, Founder and Group CEO, Digital Web Solutions
Conduct Seasonal On-Site Reviews
Running Exterior Alliance for nearly a decade across Dublin and Greater Columbus, I’ve found that leadership cannot effectively support exterior crews from behind an office desk.
A specific practice we implement is having our managers conduct seasonal, on-site installation reviews alongside our field crews during challenging weather transitions, such as managing cold-weather siding acclimation.
Experiencing the physical demands of Ohio freeze-thaw conditions and safety protocols gives our leaders direct insight into the daily hurdles our installers face.
When leaders witness those field realities up close, they are far better equipped to adjust safety standards, invest in the right equipment, and genuinely support our team’s growth.
Daniel Blanton, Owner, Exterior Alliance
Bring Frontline Insights to Discussions
Another approach we employ is the encouragement of leaders to get involved in front-line discussions and listen to employees about what makes their work difficult instead of basing our decisions on the information received in management reports. Our objective here is to gather information on the challenges faced by employees.
We encourage leaders to introduce one piece of information gained during front-line discussion in the course of leadership discussion. This will develop a simple way of linking strategy to the reality experienced by employees.
George Fironov, Co-Founder & CEO, Talmatic
Rotate Leaders Into Client Calls
One practice we implemented is having leadership sit in on actual client calls and account reviews periodically, not just review summaries or reports secondhand. When we were smaller, this happened naturally, but as the team grew, leadership started getting distanced from what was actually happening day to day in client accounts, relying on dashboards and status updates instead of hearing directly what account managers were running into.
We fixed this by setting a simple rule: leadership rotates into at least one live client call per week that they’re not directly managing, purely to listen, not to run the call. It’s not a formal review, just presence. The goal was to hear the actual friction—a client pushing back on something, an account manager improvising a solution in real time—before it got summarized and smoothed out in a written update afterward.
The impact showed up in decisions that used to be made from a distance. Leadership started catching patterns across accounts that individual account managers wouldn’t necessarily flag on their own, since each person only sees their own client, but a leader sitting in on a few calls a week started noticing the same friction point coming up across different accounts. That directly shaped a couple of product and process changes that came from what leadership actually heard, not from what got filtered into a report, and it kept the team’s day-to-day reality from getting lost the more the company grew.
Ankita Pathak, Founder, OneMetrik
Make Leaders Write Awards
The practice that changed the most for us was making leaders write the award, not just hand it out. When a VP has to name what somebody actually did, in 1 or 2 sentences, they cannot do it from a dashboard. They have to call the supervisor, and sometimes the person themselves. We ask every leader to write 2 of those a month. It takes maybe 20 minutes, and it forces a real conversation with somebody 4 levels down that would not have happened otherwise.
The failure mode I see most often is leaders who delegate recognition entirely to HR. The award still goes out, the employee still gets a plaque, and nothing about the relationship changes. The value is not in the item. It is in a senior person having to learn enough about the work to say something true about it.
Vincent Nero, VP General Manager, Successories
Require Firsthand Problem Reports
Every leadership meeting opens with one unresolved frontline problem, brought in by the leader who heard it firsthand and told in the employee’s own words. I want the actual sentence somebody said while doing the job, not a summary passed up through a middle layer.
I came to that from running group sourcing events for entrepreneurs. Whoever plans the day has to be in the room where the work is happening. When I plan it from a distance, I end up designing around what should be happening.
The moment I’m physically alongside people doing the work, the friction shows up in the first hour and the plan changes on the spot. Building and launching AI products on my own, I am the frontline. Every clumsy step, every confusing screen, everything that takes four clicks instead of one lands on me directly.
So I make the loop a requirement. A leader who arrives with no frontline problem in hand hasn’t been close enough that month, and I name that out loud. Then the problem gets an owner and a date before the meeting moves on.
Will Mitchell, Founder, StartupBros
Present Raw Employee Words
Frontline people have nothing to hide. They just take the sharp edges off the story on the way up, just as we all do when we talk to the person above us. The managers then take the sharp edges off their director’s version of it.
By the time it lands at a leadership meeting, it’s been through three compressions of relatively sensible softening and arrives as a slide labelled ‘overall sentiment positive; concerns about workload’.
So the rule we have adopted is that no one presents a summary of what frontline people think; they present the actual words. Their own screenshots, the text from a ticket, the message some poor person sent at 11pm – word for word, unsanitised, even the unfair bit. The difficult part is getting leaders to buy into it, and they offer entirely practical-sounding objections. That’s not scalable. That’s anecdotal. One angry message is not data. They are all completely valid. And yet…
The summary was never data. It was someone else’s compressions of exactly the same anecdotes. What I would not pretend is that this fixes everything alone.
It only works if something can demonstrably be seen to change as a result of one or other of the raw quotes, so when you refer back to the comments you can explain why.
Otherwise you’ve simply created a more efficient way to gather gripes, and we won’t get a second round of raw honesty.
Abhishek Shah, Founder, Testlify