Creating a culture of continuous feedback in a remote environment with Shelby Wolpa

Proven strategies for creating feedback loops at work.

New World of Work logo alongside Shelby Wolpa's headshot

Welcome to New World of Work: a podcast exploring the new frontier of the modern workforce. In each episode, we’ll hear from some of the world’s best and brightest people and culture experts on the cutting-edge topics HR professionals are most interested in today, explored through a global lens.

Episode description

Sharing feedback with an employee isn’t always everyone’s favorite task, especially if that feedback happens to be less than stellar. As many of us move into full-time hybrid roles and the war for talent rages on, it’s more important than ever to ensure teams are operating on a solid foundation of trust, respect and mutual understanding. In this episode of New World of Work, Rhys sits down with Shelby Wolpa, the founder of Shelby Wolpa Consulting, for a discussion on how people operations leaders can build a culture of continuous feedback to ensure employees remain fulfilled and satisfied in their roles, while performance issues are addressed quickly and smoothly. With over 15 years of experience in people operations, leading the charge at companies like InVision and InstaCart, Shelby now advises top CEOs, people leaders and venture capital firms to help them in their journey towards becoming people-first organizations. During the episode, Shelby shares her tips and proven strategies for cultivating an environment of continuous feedback at work.

Episode transcript

Rhys: Welcome to New World of Work: a podcast exploring the new frontier of the modern workforce. 

I’m Rhys Black, Head of Remote at Oyster, a global people operations platform making it easier than ever to build a brilliant team on an international scale.

On New World of Work, we’ll hear from some of the world’s best and brightest people and culture experts on cutting-edge topics that people ops professionals need to hear today, all through a global lens. 

Join us as we navigate this new world of work together and learn more about each other along the way. 

Sharing feedback with an employee isn’t always everyone’s favorite task—especially if that feedback happens to be less than stellar.

As many of us move into full-time hybrid roles and the war for talent rages on, it’s more important than   ever to ensure teams are operating on a solid foundation of trust, respect and mutual understanding.

Building a culture of continuous feedback is one way to ensure employees remain fulfilled and satisfied in their roles, while performance issues are addressed quickly and smoothly. 

To discuss proven strategies for cultivating an environment of continuous feedback at work, I’m sitting down  with Shelby Wolpa, the founder of Shelby Wolpa Consulting.  

With over 15 years experience in people operations, leading the charge at companies like InVision and InstaCart, Shelby now advises top CEOs, people leaders and venture capital firms to help them in their journey towards becoming people-first organizations.

Shelby kicked off the episode by sharing more about her career background so far including what led her to launching her own consulting business and her overall approach to people ops.

Shelby: So over the last 15 years, I've been a people leader at four venture backed companies that have scaled to unicorn status where I built and led the people strategy through hypergrowth. My strength really is coming into a company around 100 employees and building the people team and the people strategy from the ground up, all while the company is going through hypergrowth, typically growing the company from 100 to 500 and then over 1000 employees. Prior to starting my consulting business, I was the VP of people operations at Envision, which was a fully distributed company. Years before the pandemic. So at Envision, I supported the company's growth from 200 to 800 employees, where everyone was working remotely from their homes across 30 countries around the world and 40 states across the US. I wasn't intending to join Invasion after I had done three hypergrowth unicorns, but couldn't miss the chance to build a best in class culture at scale in a fully remote company.

So what led to me starting my own consulting business was that when the pandemic hit in the entire world went remote, companies were scrambling to figure out how to shift gears and support their remote workforces. I was ready to leave and vision and saw an opportunity to take all the experience that I had learned there. Plus, at my prior companies, being a people leader in share those learnings with as many startups as I could. So in late 2020, I started my consulting business, where I now advise CEOs, people, leaders and venture capital firms on people strategy and remote and distributed work. Since starting the business, I've had the opportunity to support many companies through their transition of going from being an in-office culture to a remote first or fully remote culture. And my clients really range across many industries. So although my background is largely in software or technology, I have companies in health, tech, e-commerce, data analytics, real estate and more. I find that regardless of the industry, that many companies are experiencing the same challenges when converting to remote first. [00:04:39][90.6]

So the mission of my consulting business and where I focus my energy is that many companies were forced to become remote companies but didn't choose to work this way. When I was at Envision, we all opted in to that remote work experience. But many people have struggled and many companies have struggled to find their way. So for the companies considering offering some form of remote work flexibility for the long term, they need to recognize that there are fundamental changes that are needed to inform how their organization operates. So the one requirement that I actually have with the clients that they that I take on is that they are fully embracing remote first and that the entire leadership team is bought into that strategy. I view it, as you know any other how you would approach any other major organizational change in a business that I want the entire leadership team bought in to shifting their culture. And that takes commitment. Trial and error in a constant focus on measuring, listening, learning and iterating.

When I work with my clients, there is a fair amount of education involved and change management for the leadership team and the entire organization. So when I talked about listening and learning and iterating, I will typically put in place a series of surveys and focus groups all throughout that journey of transformation so that we are constantly listening and checking in and making sure that we are, you know, designing something that's right for that individual company and not just a copy and paste of, you know, what they've seen. Another company do.

I support companies in a number of ways. My core offering is my advisory work supporting clients on an ongoing advisory basis on their people and remote work strategy. But I work very deeply with those clients over a series of many months, and so I'm limited on the number of clients that I can take on at any given time, given I may one woman business. But I know that there are many startups out there struggling and that could benefit from, you know, learnings that I have to share. So I've been working on ways that I can scale myself and scale my business in one of those ways is that I recently launched an initiative to package my best practices that I've learned throughout my career on a number of topics into playbooks that any startup can purchase. And these encompass all the trial and error and all the learning of how to do it wrong so that startups can leapfrog their maturity and or just get fresh ideas if they need a refresh of a current program. So these playbooks can be purchased on my website and covers such topics as remote onboarding, creating a culture of continuous feedback off boarding and other topics. I also have a free guide available for anyone to download that really focuses on the foundational aspects of building a remote first company culture. So if you're just curious about kind of thinking through what operating model works for your company and what steps you may need to think through on the employee experience side, I would recommend starting with that free guide as a great baseline for your transformation. And finally, for companies that don't need ongoing coaching but are looking for quick advice or kind of a one off conversation with me just to get them started, I offer ask me anything micro consulting sessions. So similar to the playbooks any startup can go on my website and book time with me, and I will fill that time with as much value and learnings as I can.

My overall approach to people leadership is that I believe that people first cultures drive successful companies. And what I mean by people first is that I prefer to work with companies whose founders believe wholeheartedly that their talent is their most important asset and design the employee experience and culture to support that belief. I've been exposed to companies where employees are not viewed that way, and they are viewed more as a row on a spreadsheet or as a cost center, and I prefer to not be affiliated with companies like that and because I believe that that leads to poor outcomes.

Rhys: Shelby’s people-first approach is reflective of the belief that talent is any company’s most important asset. Treating your employees like a number isn’t an effective strategy for talent retention, to say the least.

And in the current climate we find ourselves in, companies can’t afford to lose key team members. Thankfully, more and more leaders seem to be coming around to the people-first philosophy, especially within the past two years.

Shelby has watched this transformation unfold in real time, and she’s made some observations about where some companies have been led astray over the course of the remote revolution.

Shelby: I've seen a real shift in the way that CEOs are viewing their talent, given how competitive the talent market is today and how given the access to more remote jobs, there is more opportunity for employees to find great companies to work for that are outside of their geographic location. And so companies are having to think more seriously about investing in employee experience and creating a work environment that, you know, doesn't create burnout and where people feel fulfilled in their careers and in taking care of mentally. Now.

So over the last many months since I've had my consulting business where I've seen remote first transformations go awry is when the entire leadership team is not aligned on the future of work strategy. What I find is what they may say they want is not matched with the behaviors and norms of the leadership team. These norms really set the tone from the top and quickly get muddied if there isn't full alignment or if actions. You know, the kind of the the phrase actions speak louder than words. So when the so let me elaborate on that a little bit. When the world went remote, many CEOs stated they wanted to move their company to remote first or allow for hybrid work. But some CEOs are doing this for the wrong reason. They feel pressured by their employees, given that with the majority of their team has said they want or they think that going remote is the trendy thing to do and that they should do it because every other company is doing it. I believe strongly that the only way remote work can work, if, again, there's full leadership alignment. And if that way of working is weaved into the fabric of their culture, CEOs should not feel forced into going remote first if that's not what they believe in in the way that they want to work every day. Eventually, their actions will speak louder than their words, and employees will know that remote first is not truly part of the company values.

Rhys: In addition to Shelby’s people-first ideology, she’s also a firm believer in the power of a continuous feedback environment. She explained what this means to her, why she believes more companies should adopt this mindset, and how they can implement it within their own teams.

Shelby: So to me, creating a culture of continuous feedback refers to companies that frequently share feedback across all levels of the organization so that can be top down. Bottoms up, peer to peer feedback and so on. In these types of cultures, giving and receiving feedback becomes commonplace and expected from everyone. Continuous feedback has many benefits. It allows for rapid learning, iteration collaboration and serves as a strong base when enacting more formal performance reviews.

So for people, operations professionals or managers looking to create a culture of continuous feedback to me, the manager plays such a critical role in remote first companies. Managers are on the front lines observing their teams and can have such a huge impact on their engagement and retention. To me, managers are responsible for providing their teams with feedback that helps them understand where they're performing well, how to develop new skills and what they could do to perform even better in their roles. So managers delivering quality feedback on a regular basis can help their team develop new skills and perform better and propel the business further more quickly.

So creating a culture of continuous feedback can be tricky, but it's a vital skill for all remote employees to learn when you're in the same office as your team. Managers have an easier go of it where you can walk around. You can see if someone is looking off or looking tired. You can pick up on all these subtle cues much more easily. But in a remote environment, it takes far more intention in proactive behavior from managers.

So in a remote environment, people are left alone with their thoughts on a far more regular basis, and so things like imposter syndrome can creep in. Doubts, fear, anxiety, worry. Like over analyzing what a slack message meant or a comment is made in a meeting. And so to me. Continuous feedback is this amazing opportunity to push a lot of that to the side and, you know, give people clarity and confidence and waste a lot less time worrying about what their manager may think of them. So if I'm getting regular check ins with my manager, I am not sitting around worrying like what they think of me.

So providing continuous feedback in a team setting helps superpower those teams, you know, managers only know what they see. And I believe that managers should only be providing feedback on things that they directly observe anyway. So when you can get an entire team comfortable with providing peer feedback. Everyone gets more comfortable with giving and receiving feedback in those teams will thrive and they will become higher performing teams that results in bigger and better outcomes for the company overall.

Rhys: Of course, in an ideal world, a culture of continuous feedback makes sense. But what about the companies that are in stages of hypergrowth that may not necessarily have as much time to devote to the cause?

Shelby had some advice to share with companies that find themselves in this predicament but still want to capitalize on the benefits of a continuous feedback cycle. She also elaborated on the role of people ops teams in creating this kind of environment.

Shelby: Every startup that I work with is a bit chaotic and super busy. Growth brings a bit of chaos and so. It's very easy for managers and employees to feel that they're too busy for some critical moments in providing feedback. So for busy teams, my advice would be that the most important tool managers have in their toolkit is the regular one on one. One on ones should be your top priority as a manager, and canceling them should be avoided as much as possible. I'm sure we've all felt this way that when you have frequent cancelations or reschedules of your one on one with your manager, that can leave you feeling like you're not a priority, which can lead to trust issues, decreased engagement and and retention issues. The one on one should be focused on reviewing progress against goals, discussing blockers, giving and receiving feedback, providing coaching and discussing your employees development. The one on one is not for status updates. Or for the manager to get a report out on everything that their employee did over the last week. So for me. Status updates, project updates, those should all be handled asynchronously and documented in other forms in the one on one is truly for coaching, relationship building, trust building and, you know, furthering employees development.

You know, one on one's one on one should really be a two way conversation. And so if one side of the one on one is bringing the entire agenda or driving the majority of the conversation, that's usually a sign that there's a bigger issue in the relationship. I believe that remote workers do need a far bigger amount of self initiative and drive, but that the relationship with the manager needs to be 50-50. So if managers are doing all the talking or, you know, being very prescriptive in their. You know, takeaways for the one on one, I would kind of gut check that and see if there's a larger issue.

So the role that people operations can play in designing this culture of continuous feedback is to provide the tools and the templates and the programs. Did the entire company will participate in so. You know, to me, it's the job of the people operations team to select the right tool to enable this behavior at a company. I feel that in a remote organization you do need a tool and a process to find to enable that consistent, transparent feedback process. I don't think that you will be as successful if you are trying to do performance reviews or feedback in in kind of one off documents. Performance. So. Another reason that this is important to people ops professionals is that on an aggregate level, they need to be understanding, they need to have a way of understanding the performance of the organization where there are talent gaps. And use that information to drive their talent strategy, their succession planning, what learning and development programs may be needed at the company. What leadership development programs are needed. And so without having a tool to be able to pull some aggregate insights, it makes it really difficult for people operations teams to prioritize programs around this great feedback that's coming through the program.

Rhys: When it comes to addressing performance issues in a continuous feedback environment, Shelby emphasized the importance of building a solid foundation of trust across the board within the organization. 

Part of this means leaning into any awkwardness or discomfort that may arise within the team, and always assuming positive intent first.

Shelby: So. Conflict is always going to come up or performance issues will always come up, regardless of whether a company is remote or not. The best advice that I can give to remote teams and remote managers, especially, is how having mutual trust with your employees is the most important foundational step that managers can take to be successful. Great remote managers will assume positive intent when things spill off, so I can speak to my Envision experience because while I was there, I managed a large remote team and often in team meetings, I would see someone that was behaving differently in the meeting. Maybe they were, you know, quick to get upset or were short with someone interrupted someone or just seemed off to me. So as a remote manager, after the team meeting wrapped up, I would message them, asking if they could hop back on Zoom with me and just check in to see how things were going. Any time something felt off, it really is on the manager to lean in to that awkwardness or that conflict in check in on the person they may not always want to share, or they may not even know what you're talking about. But I think that it'll mean a lot to them that you care, that you took time to check in on them and then they'll know that, you know, if they do want to talk in the future that you're you're there to listen. So let's see. So when it comes to giving critical feedback or feedback, that's positive, neutral or constructive. I have many best practices to share. An easy format to provide feedback is the stop start continue format, so you can simply provide feedback using the three prompts. What's one thing this person should stop doing? What's one thing this person should start doing? And one thing this person should continue doing? And so it provides just an easy framework, especially if everyone's using this framework, it just becomes very natural. Like I've said earlier, it just becomes expected that people are going to be receiving feedback in this way, and it's a combination of highlighting someone's strengths in their areas of development. The most important advice I can share when giving critical feedback is that it should be specific. It should be tied to a tangible outcome. It should be respectful. It should be timely and ongoing. So we've all probably been there in our careers. When we receive vague feedback that doesn't have a clear call to action for how we can improve or we've received feedback way too late when we could have acted on it a lot sooner if given the chance. And then you kind of feel awkward that you've been doing that thing for many weeks or many months, and nobody has said anything to you about it. In a remote environment, I generally believe in all things that being clear is kind. Managers should stick to the facts of behavior that they directly observed if they receive feedback for it from a third party, my best advice would be for that manager to encourage that third party to bring the feedback to the individual directly. It's also probably easier to receive it from a peer than your manager, and it'll feel like a smaller deal than if your manager brings it to you. It also just is. I just think it's not best practice for a manager to bring. You know, hearsay to to a one on one, because again, they can't be very specific. If they didn't observe it directly.

Rhys: As more and more companies adopt the continuous feedback model, will there still be a place for traditional annual performance reviews and weekly one-on-ones, or will they become obsolete? 

Shelby suggests that these conventions still serve an important purpose, and if anything, a culture of continuous feedback only helps make the formal feedback sessions more accurate and data-rich.

Shelby: For me, the annual performance review is still incredibly valuable, and I encourage all of my clients to have at least one annual performance review, if not to wear. Continuous feedback is sprinkled throughout the year, with one or two touch points per for more formal documented performance reviews. The beauty of this model is that continuous performance feedback makes for a more efficient, streamlined annual performance review process. When it comes time for managers to complete an annual performance review, they can pull from the numerous data sources in conversations that they've had throughout the year to provide a more holistic, comprehensive view of an employee's performance over time. That removes a lot of the biases that we see in performance reviews today that, you know, it just becomes very difficult for a manager to think about what each individual member of their team did over a six or 12 month period.

So to me, one on ones are the most important tool managers have, and they should not be downplayed the importance of these one on ones. I believe that managers should schedule regular check ins with each member of their team starting on their first week. One on ones should be one of your top priorities as a manager in canceling them should be avoided as much as possible. When I think about cadence, most managers hold weekly one on ones for 30 to 60 Minutes. And again, it doesn't have to be weekly, it doesn't have to be 30 or 60 Minutes. You can really find a schedule that works for you and your team. But some of the things that I've observed over time is that newer employees may need more prescriptive help and more time getting up to speed in the beginning. So you may start with 60 minute one on ones and then scale back to 30 minutes once that person is ramped and highly performing in their role. I've also seen that more senior or tenured employees may need more time to discuss strategy, process improvements and career growth. So although they may be tenured, they may still need more time with you because that 60 minutes a week is going to be a high value conversation for you and the individual to give them the strategy guidance. Did they need to go off and be highly productive for that week ahead?

Rhys: Finally, Shelby shared her five to 10 year outlook of the people operations world, as well as what she’s looking forward to in her own life and career.

Shelby: When I look out at the next five to 10 years ahead, I believe that remote work flexibility and people not being tied to the nine to five traditional job or tied to a specific geographic location will continue to be the future. I personally have been living this life is kind of remote life for over six years, and I've reaped so many benefits from working this way. I am a working mom and a wife and have my consulting business. And over these past many years, I've been able to design my life creating the work life integration I need and to try to. I don't have perfect balance but do my best to to get that balance that I need in my life.

So what's what's next for me is I am on a mission to help as many companies as I can transition to become remote first cultures. Although I'm limited in the number of clients I can work with at any given time. I plan to continue sharing best practices and learnings through my website and social channels. So if you're passionate about remote work or people strategy, I would encourage you to follow me on LinkedIn. You can download my free guide or purchase some of my playbooks if they could benefit you and your organization.

Rhys: Creating a culture of continuous feedback isn’t a simple task. It takes time, effort and the conscious unlearning of traditional feedback structures. But ultimately, the extra work will pay off.  

In today’s war for talent, there’s no room for complacency. People need to be first on every company's priority list. My conversation with Shelby really helped to bring this point to life. 

Here are a few key insights I’ll be remembering from our discussion:

  • Putting people first is essential, no matter the business vertical you’re aligned with or the industry you’re operating in. As Shelby mentioned, prioritizing your talent and going out of your way to make sure they’re happy and satisfied is directly aligned with improved outcomes so it’s crucial for companies today to build this philosophy into their value systems.
  • When giving feedback, people ops leaders and managers should be mindful of their delivery. It goes without saying that feedback should be respectful, but it should also be specific and tied to a tangible outcome so that the employee can put it into action going forward.
  • One-on-ones and annual performance reviews are here to stay. Shelby suggested there’s still a place for formal feedback meetings, but they should be combined with continuous feedback to ensure a foundation of trust among teams.

Thank you for listening to New World of Work, the podcast exploring the new frontier of the modern workforce through an international lens. We hope this episode served to expand your horizons and open your mind to a new perspective.

Be sure to subscribe, rate and review the podcast so we can reach more listeners.

I’m your host, Rhys Black. See you next time.

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About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, hire, pay, manage, develop and take care of a thriving global workforce. It lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

Oyster enables hiring anywhere in the world with reliable, compliant payroll, and great local benefits and perks.

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