Chapter One: Feedback Conversations
From PIP to RIF: A four-part series tackling People & Culture topics for all markets
Recent changes in the financial markets have compelled startup founders and CEOs to go back to basics: interrogating burn rates, revising hiring plans, and refactoring organizational structures. We find ourselves in a unique moment – one that we’ve seen before as an industry, but that many founders, CEOs, and venture capitalists have yet to experience in their careers over the last decade, and certainly with a new and interesting set of extraneous variables!
Even in the most capital-rich markets though, at some point during the entrepreneurial journey, every startup founder faces the harsh reality that not only do they have the privilege of hiring amazing people, but they also have the responsibility of firing amazing people.
Both are inevitable, yet as high-growth companies hungry for talent, we often spend much more of our time focused on the former, neglecting the latter until there’s a crisis or situation in play.
In the spirit of making sound People and Culture advice accessible during this period of economic instability following ~2 years of pandemic-related workforce challenges, I’ve partnered with Carmela Krantz, Founder of Woven, a leading human resources consultancy and executive coaching practice with over 30 years of experience working with high-growth technology companies.
Though I typically write about healthcare and life sciences, I mostly write about what I find interesting or impactful at the moment. I wanted to write about these topics because they are among the most common questions I hear from founders and CEOs as an investor. Philosophically, both Carmela and I believe that by making tactical People and Culture information, which is often maintained as institutional or experiential knowledge, more accessible, we can equip startup leaders with tools to navigate what’s ahead – whatever your armchair macroeconomic view might be – with intention and grace.
Together we sought to compile and share best practices for making tough People and Culture decisions ranging from the basics of feedback conversations to full-scale reductions in force (RIFs) with the intention of bridging the knowledge gap between what you might ask your investors and/or board members for support on and what startup founders and CEOs navigate on the daily.
We hope this series empowers founders, CEOs, and managers to make decisions that center on the dignity and humanity of employees and engage through trauma-informed frameworks.
Over a four-part series, we’ll tackle the following topics:
Feedback Conversations
Performance Improvement Plan (PIP) 101
Reductions in Force (RIF): Everything You’ve Always Wanted to Know
Communicating People and Culture Information
It feels important to share that over the last five years I’ve been investing, I’ve kept tabs on what topics are escalated to board-level conversations most often. Perhaps unsurprisingly, People and Culture issues, as well as organizational growing pains are among the most common. Though institutional VC board members can be instrumental in helping founders and CEOs think through sticky People and Culture situations, many investors (save for those who led companies before becoming investors) have never managed large teams or had to fire people. In fact, many investors let people go by simply telling them they aren’t going to make Partner and they should find another firm over the next few quarters. If only it were this easy on the other side of the table!
Feedback Conversations
Carmela and I are excited to kick this series off with what we consider to be the foundation of any functional working (or otherwise) relationship: feedback conversations. Before diving in, let’s define feedback in the context of a job:
Feedback is a conversation where people share information in anticipation of a better outcome. Sometimes there is tension, but the better outcome usually makes it worth it.
Successful feedback conversations can result in many different outcomes, two of which are most desirable:
An employee or colleague accepts the feedback and adjusts
An employee or colleague accepts the feedback and decides the organization is no longer a good fit
Arriving at one of the two desired outcomes – those that are best for the employee and company at the end of the day – starts with the feedback conversation.
Who taught you “how to give feedback?” Who taught you “how to receive it?”
For many of us, especially those who have yet to engage in formal executive or managerial training, we learned the skill of providing feedback based on our own experiences receiving it in personal and professional relationships. This lack of structure around developing a “feedback practice” has allowed sub-optimal methods to replicate and persist.
Despite the near-infinite ways it feels like feedback conversations could go wrong, at the core, they are formulaic. In this piece, we offer a few attributes of feedback practices that can increase the likelihood of successful conversations. Note that throughout our series, we do not use the phrases “giving feedback” or “receiving feedback”; instead, we use Feedback Conversations.
Why? There is an inherent power dynamic in giving and receiving, which is often unproductive. Subtle shifts in language that frame feedback as a multi-stakeholder conversation can go a long way in setting the table for a productive discussion.
First, make it ongoing
Convention is often an enemy of progress. The canonical practice of the annual review that many of us dread or at best feel neutral about has created a dynamic where feedback conversations “off-cycle” can feel uncomfortable or rogue for managers and employees alike. For managers, constructive feedback conversations are a top cause of discomfort when communicating with employees. It’s often easier to wait until the formal review period when everyone at the company is engaging in feedback conversations to share a list of grievances about everything a colleague has done wrong.
For employees, asking for feedback often feels like you’re creating a burden for your manager, who is already busy with everything else going on in their role – will they be annoyed if you ask outside of the existing process? For what it’s worth, if your manager ever seems annoyed that you’re asking for feedback more than once a year, you should probably find a new manager… but that thread merits an entirely separate post.
When we talk about ongoing feedback conversations, we’re referring to discussions about what’s going well in addition to what could be going better. For conversations about what’s going well, it can be helpful to frame the discussion around “Let’s do more of this” or “How did we get here? Can we replicate it?” A tangential benefit of discussing both areas of strength and improvement is that during ongoing feedback conversations, people receive recognition for a job well done.
Feedback conversations are a key part of startup culture. Any dynamics that delay or reduce opportunities for feedback conversations are harmful, and in fact, are antithetical to the core principles of startup culture where we ground ourselves in short, parallelized interaction cycles in the spirit of learning and growing quickly. Most often, startups apply principles of learning and growing quickly to products being brought to market. We suggest that startup principles of learning and growing quickly also find applications in the People function to serve the humans behind the products.
Imagine if you only received feedback once a year for the rest of your life. How much better off would you be if you received it quarterly? Monthly? Even weekly?
So, the first part of developing a strong feedback practice is engaging in feedback conversations on an ongoing basis. How frequent is it ongoing? The recurring cadence is for you to determine, but in general, we like to abide by the 24-48 rule:
This could mean that you reach out within 48 hours to find a time over the next week to discuss your feedback, and in the next section, we’ll touch on how to tee up the conversation thoughtfully.
The major benefit of creating a practice of ongoing feedback is that any time there is a need for constructive feedback, it won’t come as a surprise. Ongoing feedback loops help both managers and employees feel more comfortable engaging in conversations around performance – the more you do it, the less awkward it becomes. Additionally, talking through challenging topics with regularity can help people develop the tools and practices to have hard conversations downstream; for example, talking about working with difficult colleagues, holding people accountable, and delivering tough news to a colleague.
We recognize the focus of this article is feedback conversations in the context of manager-employee relationships, but hopefully, so far, it’s clear that it can be beneficial to implement these practices in many types of professional relationships including peer-to-peer and mentor-mentee, as well as personal. Oftentimes, these other relationships offer fertile ground for practice and honing feedback skills. We’ll address best practices for employees to instantiate feedback conversations with managers later in the article.
Kicking off the feedback conversation tactically
Framing the feedback conversation as a conversation is key. When reaching out to make time to discuss feedback, it’s important to maintain clear and direct communication that centers on intention and goals for the conversation. For constructive feedback, broaching the topic can be as simple as saying something along the lines of:
“I want to share an area of concern I have…”
“I want to discuss a particular behavior that I’d like to see you work on, and understand how I can support you in that work”
Starting by setting expectations about what you’re going to talk about and why you’re talking about it is critical. The whole purpose of engaging in a conversation is to make sure that people come to the conversation with prepared minds in order to increase the likelihood that they leave the conversation (both the manager and the employee) with a clear understanding of what went wrong or what performance is falling short, and where to go from here.
How do you know when constructive feedback is warranted? Here are a few classic signs to look out for:
When an employee is repeatedly missing deadlines and/or pre-established performance objectives.
Depending on the role, a feedback conversation might happen after one miss or might happen after several misses (e.g., sales reps who operate quarterly...how does each month’s performance impact the quarter?)
When you, as a manager, have received complaints from colleagues about an employee.
Typically, feedback conversations take on a four-part structure:
1. Tell them what the problem is!
During this part of the conversation, specificity is key. What are the actions and behaviors that you’ve observed or experienced that pose reason for mention or concern? What opportunities exist for improvement? One of the major impediments to having a productive feedback conversation is that many people never learn how to have direct and specific conversations in professional settings and fear that by being direct, they might hurt someone’s feelings or make them upset.
Do not soften the blow, and whatever you do, refrain from the dreaded but sandwich – “Thanks for this....it was great, but you weren’t skilled at that, and don't forget you were good at this.”
When we stop thinking about and referring to these conversations as “a blow,” it makes people less anxious to have them. Besides, “the blow” feeds the power dynamic, and we’re trying to move away from that. In reality, the power dynamic never fully goes away as most of us have a boss or manager, but we can reduce it somewhat by how we approach these conversations.
For these reasons, as a manager, it’s also important to give feedback early and often so that you and your employees are used to having direct conversations about areas of development. In reality, feedback is a gift, and so managers that are vague or dilute observations (e.g., behavioral issues, performance issues) are doing a disservice to their colleagues and often leave folks feeling confused by the conversation. Be sure to talk about the specific behaviors and not the person.
2. Tell them what the consequences are.
After explaining what the problem is, explain the downstream impacts. So if you do x, it supports the team. It supports our business outcomes. It helps drive our business outcomes. If you don't do x or you do y instead, it has a negative impact on our business objectives or outcomes, etc. As an example, an engineer that repeatedly fails to push code in a previously agreed-upon timeframe might leave the rest of the team in a position where they are unable to do their parts if there is a blocker earlier in the software development process. Other examples across functional areas might be delayed client or prospect communication or consistent internal communication across teams.
3. Offer them an opportunity to share.
After explaining the problem and downstream consequences, invite the employee to join the conversation. You can do this simply by asking questions like:
“What do you think about this?”
"Can you tell me what you heard my concerns are?"
“Does this feel like an accurate summary of where you are?”
"Is there anything I am unaware of in this situation?"
“Is this an accurate articulation of where you’ve been performing and where there is opportunity to improve?”
Inviting the person to participate in the conversation creates opportunities to understand their experiences, identify any impediments that might be impacting their ability to perform in the areas you surfaced, and ensure that they heard your feedback accurately.
4. Identify next steps.
Before leaving the conversation, make sure that both parties are aligned on what’s happening next. This part of the conversation is about operationalizing the feedback. It’s the manager’s responsibility to come prepared with some ideas about what the solutions could look like; however, before offering these ideas, it’s best if the manager can ask the employee what ideas they have – i.e., “do you have any ideas about how you might work on this or improve this?” Examples of the next steps include:
Setting up another meeting in the future to check in about progress against goals
Engaging other members of a team to assist as accountability partners by communicating what the employee will be focusing on
Flexibility is integral to the success of the next steps after a feedback conversation. Consider asking what format works best (e.g., in-person, phone, video) and what cadence (e.g., weekly, monthly, one-off, etc.). You can always amend these parameters if they are not working in the future, but it’s helpful to empower the employee to chart the path forward towards improvement so they feel, and actually are, bought in.
Feedback Conversations with your Manager
We’ve mostly covered the art and science of the feedback conversation when a manager is discussing feedback with an employee. How might you handle a conversation when you are discussing feedback with someone senior to you? Many of the same guidelines apply when you seek to have a feedback conversation with your manager, for example:
Don’t wait – 24-48 rule applies!
Have the conversation privately and avoid having the discussion with other team members present
Invite your manager into a conversation – “would you be open to having a conversation about x?”
Start the conversation from a place of curiosity: “I’d like to learn more about x as I may have some insight to offer…”
Prepare for the conversation with facts and/or data to support your position
Don’t get personal about the manager or other colleagues; instead, focus on behaviors and outcomes
Agree on the next steps with your manager as a means of unlocking improvement and accountability
Be courageous, if necessary (see our aforementioned comment about getting a new manager)
When a manager sets the tone that feedback conversations are important to them by initiating them, they have an opportunity to invite feedback conversations from team members. The best managers will directly ask employees to engage in reciprocal feedback conversations; however, if this isn’t the case, you can show that you are committed to engaging in feedback conversations bidirectionally by starting them on your own. If your manager appreciates the value of feedback and sees it as the gift that we know it to be, they’ll be grateful.
Should you document feedback conversations?
Before having a feedback conversation, you might be wondering whether it’s something worth documenting, and if so, how? If it’s an initial conversation, we advise managers to make a note in their calendar that they had the conversation with the employee on a certain date, in case they need to refer back to it at another time. If it’s the second or third time that the feedback conversation has happened on a particular topic, it may be time to document the conversation in the form of a Performance Improvement Plan (PIP). We’ll be doing a deep dive into PIPs for our next piece!
Final Thoughts on Best Practices for Feedback Conversations
Many managers and employees establish recurring meetings for feedback that are pre-set on the calendar for many months and quarters in advance. Though this might not work for everyone, we like the premise of a monthly performance conversation as it ensures that any feedback that slipped through the 24-48 rule can be addressed in a timely manner.
At the end of the day, people only change because they want to change and because they're motivated to change from within. Feedback conversations are an important catalyst for intrinsically motivated change. We hope this piece helped shed some light on how you can engage in productive feedback conversations and look forward to diving into simple and effective Performance Improvement Plans in our next piece.
Subscribe here to get the rest of the “From PIP to RIF” series delivered to your inbox, and check out Woven’s website to learn more about Carmela’s practice.
Thanks for reading!
Morgan and Carmela
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Special thanks to Nikhil Krishnan for reading drafts of this!
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