Patrick McKendry

This past week, the world celebrated Valentine’s Day, a holiday for our nearest and dearest relationships. The holiday has its origins in Christian feast days commemorating the saint and early martyr, Valentine. However, the date has held its significance as a romantic holiday for hundreds of years. Traditions of sending cards can be traced back to 1797 when a British publisher produced The Young Man’s Valentine Writer that contained a selection of pre-written poems for sharing by those less articulate with their emotions. Cadbury introduced Fancy Boxes in 1868, a heart-shaped box of chocolates, which gave way to all varieties of gift exchanges on the holiday. Today, it is estimated that the average American spends $131 every year on Valentine’s cards and that around 190 million valentines in total are sent each year.¹

You might be wondering how a holiday celebrating our closest personal relationships has a tie-in to a work blog. Simply, when we think about important relationships, there is one connection that gets consistently overlooked and under-analyzed. Our manager is, in most cases, the one person with the greatest impact on our career.² The healthiness of our relationship with them can have direct impacts on the job opportunities provided to us, the amount of stress and friction in our day-to-day activities, and the quality of feedback we get to support our growth.³

Yet, much of the literature on developing a healthy relationship with a boss is incomplete. For example, many articles - like this one from HBR - focus on establishing a vision for the relationship and having a tactical action plan for when and how you will communicate.⁴ If we think about our personal relationships, that advice feels inadequate for creating something robust. Imagine if we applied that advice with a significant other and only went so far as to build a plan of what we wanted the relationship to become and how often we intended to talk. It might work, but it definitely leaves a lot unclarified.

Instead, let us turn the tables and apply some of the top advice on building quality personal relationships to our professional lives.⁵ While our professional relationship should ALWAYS maintain an appropriate distinction and separation from our personal lives, we should note that as social creatures, human behaviors that foster effective collaboration will show themselves across social constructs. We will look at guidance from certified therapists and clinicians for operating healthy relationships and then see how that can tactically apply to building highly effective working interactions with our boss.

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“Schedule dates to talk about your relationship.”

“Commit to investing an hour—on an ongoing basis—to work on strengthening your relationship, troubleshooting, and making it more satisfying,”
- Joseph Cilona, Psy.D., Licensed Clinical Psychologist

Any effective relationship should take dedicated time to reflect on what is going well and what can be improved. Most people have a 1:1 with their manager. For some, these meetings are ineffective at nurturing collaboration and productive feedback. When these meetings go wrong, there are a few common reasons.

First, these go wrong when they are not consistent or frequent. Imagine if we thought about the health of our personal relationships only bi-weekly or monthly. Topics can easily come and go and be forgotten at that cadence. Default to a weekly occurrence and keep it. It can sometimes be tempting to cancel a 1:1 if it seems like there are no pressing items. This can be a slippery slope that drives the meeting to become too infrequent to be useful. Managers this requirement mostly sits with you - don’t slip up.

Second, 1:1s are worse when they are not focused on the relationship. Many managers will use a 1:1 as a check-in on work priorities. It is certainly important to keep aligned on what work is being done, but I recommend keeping this to a separate meeting focused exclusively on that topic. When priority discussions are introduced to 1:1s, they quickly grow to dominate the recurring conversation because these items are more comfortable to talk about and are always present. However, the style of conversation is also very different between priority discussions and talking about interpersonal dynamics. Switching back and forth can be hard. Instead, the expectation should be that the 1:1 topics are focused evenly between personal development for the direct report and the relationship between the two people. This is easy to set-up by the manager, but the direct report can also introduce this expectation. They can do this by clarifying that they want to “help ensure they are getting you (the manager) the things you need and in the format that is most useful to you.”

Third, a 1:1 is incomplete when it is one-sided. I have heard of many cases when managers introduce 1:1 meetings by stating “This is your time. I expect you to bring the problems and questions you want to cover.” Just as frequently I talk with direct reports who say “I know my manager has the things they want to cover so that is what we talk about.” Our personal relationships would fall apart if we followed this model. If one party brought up all of the problems, each person would begin to resent the other - either for always bringing up problems or for never seeming to care enough to bring up problems. In our 1:1s, as the one-sided topic default becomes entrenched, any effort by the normally passive party would seem out of place and take on an undue significance because of its unexpected nature. As a result, smaller discussions that could establish a more even balance likely are abandoned in this less psychologically safe environment. Instead, set the expectation for your 1:1s that each side should bring topics. Again, this is easy if you are the manager. As a direct report, you can prime the conversation by asking for feedback and, after receiving it, stating for your manager that it would be helpful if they could bring feedback like this each week.

Establishing a cadence for review is an important foundational step that creates space for the other recommendations we will cover. The key to making 1:1 meetings effective is to be intentional with the time. Keeping the time consistent establishes its importance above other work distractions. Clarifying the topic goals at the outset can set up the meeting for ongoing relevance. Putting the onus on both people to bring topics can ensure that discussion is robust and properly covers all aspects of the manager-direct report relationship. Start by establishing a good 1:1 practice. Then, build on top of that foundation.

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“Fight in a productive way.”

“When we begin shifting our language to share how our partner's behavior makes us feel rather than just telling them what to do, I find that couples become more fluid and more aligned in their daily functioning,”
- Jennifer L. Silvershein, L.C.S.W., Psychotherapist

I use this advice a lot, particularly to broach difficult or sensitive topics. It is a cheat code. There is almost nothing as counterproductive as when someone proactively gives us tactical feedback or recommendations based on an incorrect assumption of why we are doing things or with incomplete information of our context. We immediately disregard the feedback because we know it will not solve our context-specific problems. Further, we may feel resentment towards the manager/mentor for not bothering to fully understand our situation. And we may feel isolated by the fact that others do not clearly understand what we are working through.

For managers, grounding the conversation in well-intentioned interest to understand is a highly effective way of working towards giving better advice. Starting this conversation is as easy as sharing your feelings. Your feelings and perceptions are an indisputable truth that you know definitively. Start with “I feel like…” or “I am sensing that…” in order to ground the conversation solely in what you know. Then, follow with insight seeking comments like “I feel like I’m missing something, am I?” or “I’m sure there are other things at play though”. This demonstrates that you are looking to better understand the other person’s situation and stresses to them that you have a genuine desire to help because you are not just tossing out low-context recommendations. It also gives the other person the chance to collaborate with you on the solution.

For direct reports, this can offer a low-risk way to initiate upward feedback. With this framing, you can introduce ideas less as advice and more so as information. For example, if your manager tends to hold onto project context when they get stressed you could highlight that “I feel like you seem stressed, but I can’t tell if its related to the project and I can help or if it's just something outside of work”. If it is project related and your manager willingly gives more detail, you can then follow-up with the feedback that you have consistently noticed that they often forget to communicate downwards when they are stressed. This is important guidance for them to hear, and sharing your feelings first can make it easier to bring up.

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“Be candid about your feelings—the good and the bad.”

“Once you think that your feelings don’t matter, won’t be heard, or are not worth sharing, you open the door to harbor negativity and resentment.”
- Beth Sonnenberg, L.C.S.W., Psychotherapist

This may go without saying, but you need to talk about both good and bad things. Talking about the good things means thanking your manager for being timely with their feedback after every meeting presentation and highlighting a direct report’s good work in building a data visualization to update the executive team. This appreciation goes a long way in establishing ongoing good behavior and creates motivation and momentum for the team.

As the manager, talking about problems is also important and can be easy. The key here is that you discuss them in an open-minded way where you work with your direct report on defining the best path towards improving. This approach shows that it is healthy and expected to talk about what is not going well and that you are interested in working to mutually beneficial solutions.

As the direct report, talking about bad things means calling out questions that your manager is asking that are distractions to the team, frustrations over organizational processes that are slowing you down, and addressing low motivation caused by not learning new skills. Often, we feel like we should not bring up difficult conversations because we are generally happy in our role and do not want to be perceived as a problem. When we do not talk about what is going poorly, we will inevitably grow to be unhappy in our role and become resentful. Most managers have good intentions and want to help you be happy and fulfilled in your role. By highlighting opportunities, you make it easy for them to help you. When you address these concerns early and regularly, you keep the conversation from becoming difficult and prevent negative feelings from growing out of hand.

Low psychological safety tends to be the common underlying cause of why we do not speak openly or directly about problems. Humans are social creatures and are biased to fitting in, building up the community, and maintaining positive relationships. The natural action for most teams will be to conform with the plans and approaches that the leader has defined. To overcome this natural bias, leaders should build environments that promote psychological safety amongst their team. This means framing work as a learning problem rather than an execution problem, acknowledging your own fallibility as a leader, and modeling curiosity and asking questions.

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“Don’t expect your partner to be your BFF.”

“We expect so much from our relationships these days. We want our partner to be a best friend, confidant, co-parent, and companion. Yet, this sets us up to be disappointed when our partner cannot fulfill our needs,"
- David Klow, Licensed Family Therapist

For some people this may go without saying, but your manager does not have to be your friend. When we talk about having a great working relationship, it is not required that you are best friends or even good friends. A relationship can be strong when it is based on mutual respect, a common goal, and open and honest communication. Workplace friends are an important source of social well-being and we should have them. For direct reports, recognize that we do not have to find that close support from a manager.

Some managers find that establishing a friendship can be an accelerator to building an effective working relationship. That is alright, but it is important to recognize that not everyone will share the same expectation and may not have a similar desire to build a friendship. Further, some people may not have the same sense that a friendship should enable critical feedback and become surprised when difficult workplace conversations are brought forward. At all times, keep the goals of your manager-direct report relationship top-of-mind and clear for both parties. For managers, work to establish other effective tactics for building candor and motivation while also practicing maintaining individual boundaries.

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“Before commenting, repeat their words out loud.”

“You will be endlessly surprised at how the simplest statements are heard differently by various people. This not only dramatically improves the accuracy and quality of communication by allowing for correction of misinterpretations, but also creates [a] strong sense of being heard and understood in each partner.”
- Joseph Cilona, Psy.D., Licensed Clinical Psychologist

Our perceptions are an outcome of our individual experiences collected over time and our immediate focus in a given situation. A simple statement to our manager like “I think I can take on larger projects” could be interpreted in a number of different ways. If the manager has previously had people take roles elsewhere when they became bored, this statement could throw them onto high alert. Or, it could remind them of a time where a pretentious employee sought out a higher title despite not delivering on their existing responsibilities. Your intent may be harmless as you simply look to help out while you have some extra capacity.

For managers, this complexity of perception in the human experience shows why it is useful to ensure you are on the same page before you get to problem solving. I frequently use the phrase “Let me say this back to you to make sure I’m understanding you”. Conversely, I prompt my team with “I just said a lot, say that back to me so I can make sure I was clear”. As noted by Cilona, this creates the space to correct any misperception and make sure that you are both pointed clearly at the main point of concern. Further, it displays active listening and a desire to fully understand and be understood. So many times, the key factor in working through a difficult situation is just building the resilience to get through it. For our directs, feeling heard and seen by a manager can be the difference between making it through versus burning out.

For direct reports, this advice is relevant far more often and far more importantly. Managers regularly give feedback. However, that feedback is shaded by what they have seen from your behavior and by how they think about certain skills. Before you go and implement what was recommended, stop and fully understand the feedback first. For example, if you were told that you need to be more “analytical”, how do you know whether your manager wanted you to sharpen up your statistical skills or just wanted you to better integrate numeric values into your prioritization decisions. Repeat back to your manager, what you are hearing, how you are interpreting it, and the next few intended actions you plan to implement as a result. This creates the opportunity for you both to stay fully aligned on your development plans and can give you better insight into what skill sets your manager thinks are most important and why.

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“Don't be afraid to talk about money.”

“A couple that communicates their financial goals, and is willing to work together to achieve them, will likely have a deeper bond,"
- Joseph Cilona, Psy.D., Licensed Clinical Psychologist

One of the most overwrought conversations in both our professional and personal relationships is around financial goals. While discussing finances can deepen a personal relationship, it really should be table stakes for our relationship with our manager. As we have covered, a healthy managerial relationship is a key differentiator in our career success and our career success should be the primary goal for our manager. As such, talking about goals for both promotion and compensation and aligning on plans here can pay-off in multiples. Yet, most of these conversations are limited exclusively to the annual review process.

As a manager, you should set-up this conversation with your direct report and discuss it regularly in a structured format. I recommend an IDP - individual development plan - as a tool for this conversation. In an IDP, both parties align on career goals to start and put together an overview of key development opportunities and tactical behaviors that will deliver that growth. The plan should be reviewed regularly, at least once per month. For managers, the tool can provide clear expectations of what is needed to be delivered to set the employee up for financial growth.

For a direct report, the IDP is a great tool to talk about compensation. It provides the structure for comparing work against job requirements and title expectations. It can lead to the conversation on performance and compensation comparisons versus a peer set. Importantly, the overview becomes based on objective performance delivery and a regular cadence, which desensitizes the request and demonstrates one’s willingness to work towards their compensation increases.

Again, let me highlight that the promotion and compensation conversation should not be a weighted one. Both parties should be aligned on a similar goal of individual growth with proportionally reciprocated value for the work delivered. In cases where this is not happening and not discussed, the only viable path forward is to talk it out.

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Relationships are core to the human experience. They are the atomic foundations of societies at large and communities at a smaller scale. For many of us, our personal relationships are among the most significant parts of our lives. Relationships are in their own way a force of nature, with their influence developing over millions of years alongside humanity itself. All of which to say, relationships are an incredibly powerful tool. When we move past seeing our managerial collaboration as a haphazard pairing, we can think more deeply about the thoroughly researched and successfully practiced tactics that go into building highly effective relationships. Many of those tactics can apply to our professional work. When used thoughtfully, they can help build more effective collaborative, results-focused, and human organizations.

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References

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Relationship Advice - How to Work Most Effectively with your Boss

“Schedule dates to talk about your relationship.”

“Commit to investing an hour—on an ongoing basis—to work on strengthening your relationship, troubleshooting, and making it more satisfying,” - Joseph Cilona, Psy.D., Licensed Clinical Psychologist