Browsed by
Tag: getting feedback

Should I speak up and voice my thought?

Should I speak up and voice my thought?

I’ve definitely had strong thoughts about things at work, and yet kept them to myself.

In many instances, it was absolutely the right thing to do (e.g. when I’m frustrated at a client), but in other cases, it was most likely counter-productive. Especially in a startup environment, it’s my opinion that ideas need to flow freely. 

So in this blog post, I’m going to explore a few situations where not voicing our thought can be detrimental to the company:

“That’s a good point… now I don’t need to bring it up anymore.”

My process for reviewing product plans goes something like this: 1. Review the entire plan; and 2. Give feedback that others haven’t given yet (e.g. ask about how my team will be impacted).

What I fail to do is show support for other people’s thoughts and feedback with +1’s.

That hurt us bad one time:

After reviewing the plan for a new product feature, I noticed a comment that a colleague put in: “The design team failed to gather input from the customer success team, which would eventually have to use and educate our clients on the new feature.”

I agreed entirely with that comment, but didn’t show my support. My colleague ended up being the only one that voiced that concern.

So guess what happened… They designed and launched the feature without input from customer success. It resulted in flaws that caused some frustrations among users at launch. There’s a high chance that it could have been avoided by simply including the CS team in the product design process. That wasn’t the only negative outcome either. By neglecting their input, the customer success team had also lost a good amount of trust in the design team.

Speaking with the design team leader over the issue, it became clear that they didn’t get feedback from customer success because they thought that it wasn’t as important as some other issues. Afterall, only one person voiced the opinion that CS feedback was warranted.

So what did I learn? That +1s are important. People gauge the priority of issues by evaluating how much support it has.

“I don’t think they’d listen to me…”

I have dozens of conversations each month listening to colleagues’ frustrations about their managers and other team members. Most of the time, they’re simply venting sessions and I sit there listening. Yet on more than one occasion, people also shared with me thoughtful and well researched ideas that they didn’t share with their managers.

And when I ask them: “That’s a really good idea. Have you shared it with [manager name]?”

The answer is almost always: “No, I don’t think they’d listen to me.”

This clearly indicates that the individual lost some trust in their managerI therefore spend time helping individuals gain the confidence to voice their thought, and formulate a pitch that properly communicates their idea. We then rehearse it together and prepare against potential rebuttals.

In most instances, I’m happy to report that people find the confidence to effectively communicate their idea to their boss. Their ideas aren’t always adopted, but they always feel acknowledged and listened to. And more importantly, they learn a crucial lesson in how to influence leaders.

So if they don’t listen to us, let’s find a way to make the message more appealing and manage up.

“There’s nothing we can do about that…”

When discussing long-term or low-priority issues, I noticed a tendency for me to end a discussion with “Yeah, oh well, there’s nothing we can do about that.”

And right after, I’d feel like a naysayer rather than a problem solver. Why did I even spend time talking about the issue if there’s nothing we can do about it? Clearly I care enough and want to do something.

Yet fact is, there are situations where I’ve heard “no” to an idea so much, or witnessed the de-prioritization of an idea so often, that I think nobody cares anymore.

So how do I deal with that? With time, I’ve learned to stop complaining and take action instead. I actively discard ideas that I also feel are low-priority, but re-work how I pitch an idea that I believe is important. I may gather further evidence to support my viewpoint, or assess if other individuals and teams in the organization feel similarly to gain additional support.

This helps me avoid feeling bleak about the future, and continue fighting for ideas that matter to me.

When should I not voice my thought?

In my experience, there’s only one scenario under which an individual should not voice their thought and that’s when our emotions control the best of us.

Too often, I’ve reacted emotionally to frustrations and concerns I have with a team member. It’d usually put the individual in an awkward spot. Even if the concerns were valid, I always regretted my reaction. It’s simply unprofessional and demeaning to others, and fails to demonstrate that I can keep my cool under pressure.

How do I deal with my emotions now? I have a 24-hour rule. I don’t react for 24 hours and let a good night sleep help me think about the situation. It helps me take the emotions out of the situation, so that I can think and act rationally the next day.

Recommended exercise

Let’s identify one thought that we failed to voice this past week and find a way to communicate it.

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

Do I care about my team more than my company?

Do I care about my team more than my company?

When a start-up company scales from a core team of 10-20 team members to 100+ people, I’ve witnessed a tendency for departments to lose touch with one another. Thats when we become hyper-focused on scaling our own individual team.

This often results in the loss of cross-team communication, break-downs in collaboration, along with other inter-department conflicts.

In this blog post, I’m going to share one exercise that will help our teams avoid conflicts and stay cohesive. It starts by seeing the organization as one entity, rather than a group of separate teams.

Do I see the company as one?

Adopting this perception is critical to the success of an organization, because the alternative, to see the company as parts that work separately, will never grow the company as a whole. Allow me to elaborate:

In our day-to-day, we often view ourselves as part of one specific team, one group. In turn, we subconsciously view the organization as a group of separate entities such as marketing, sales, customer success, product management, engineering, R&D, finance, etc.

The danger of this perception is that it can create inter-team conflicts: e.g. when goals are missed, we tend to blame it on other teams; when budgets are planned, we tend to fight each other for a bigger piece of the pie.

As we don’t emotionally relate to other teams as much as we do with our own team, we focus on improving only one team: Our team. This can be detrimental. Improving only one segment of the company will not result in a better company: e.g. Hitting our sales goals may not result in higher revenue if the sales team is not collaborating with customer success on retention goals.

A company thus needs all teams to be aligned on a single strategy for it to grow. It becomes clear that improving how teams interact and work with each other is more important than improving the team itself.

In one case, I was helping a clothing retailer’s merchandising team identify product trends. The goal was to find characteristics of clothing items that people would buy as part of repeat purchases, then advertise them as part of newsletters. However, because the marketing team had differing priorities, the products we identified as leading to a higher chance of repeat purchases failed to be advertised. Instead, newsletters featured customer stories in an effort to connect emotionally with users. This is not to say that the marketing team’s tactic wasn’t effective, but because both teams failed to coordinate, time and resources were wasted. The merchandising team’s effort was in vain.

The good news is that everyone is capable of seeing the company as one. We do this every day when we look at other companies.

For example, we don’t react to news on Google’s self-driving cars and say: “Wow, the marketing team on Google’s self-driving car project is really effective at …” Instead, we say: “Wow, Google is really catching a lot of eyeballs with their cars.”

Now we only have to see our own company as a unit.

Does my team see the company as one?


To help our team members see the company as one entity, we can perform a diagnosis of the company’s traits. This translates into the creation of a profile that defines our organization and exposes our group dynamics.

Having team members evaluate the organization as one re-enforces the mindset that we are all on the same boat, regardless of what teams we work with.

One approach is to survey all team members’ perception of the organization, asking the following questions:

  • What is your perception of our company’s current vision and strategy? How do we hope to impact the world, why, and how do we plan to achieve that?
  • What are natural tendencies and behaviors that you notice of your team, other teams, and the company as a whole? What are some biases that you observe, what do we enjoy/don’t enjoy doing, what mistakes do we repeat, and what do we prioritize and de-prioritize?
  • What frustrations do you experience that gets in the way of our company achieving its strategic goals? What are you repeatedly frustrated by?
  • What do you feel are our company’s strengths and weaknesses? What helps us achieve our goals and what drags the team back?
  • What values do we live by? Based actions and behavior observed, what values do you think we stand by?

Assembling a company profile based on every team member’s perception allows for the entire company to actively reflect on what type of animal it has become. This awareness alone will make team members more empathetic to other teams. Should we take it a step further and incentivize changes while praising improvements, teams will also implement changes to eliminate behaviors they perceive as negative or unproductive.

How often should we do this and why?

I recommend for this exercise to be performed at least twice a year for a couple reasons:

  1. Start-up companies tend to get distracted by new ideas that pull teams off alignment from the company strategy, so regular assessment helps to diagnose whether any team is going off-course, and to actively re-align them;
  2. Similarly, as a company evolves, its traits change. It’s thus important to regularly assess whether the company’s behavior is evolving in the direction that we want, creating the culture that we desire.

Let’s explore these two points in more detail.

1- Aligning teams to the company strategy

one team

In my opinion, it is easier for top leadership to set a competitive strategy than it is for them to keep all teams aligned to the strategy.

Especially at start-ups, individual teams tend to get distracted by new ideas and initiatives that fall outside of the company strategy. This is caused by a combination of factors including:

  • Ambitions and smart team members that want to change the world, but are easily distracted;
  • Ineffective communication from senior leadership about the actual strategy; and
  • Lackluster enforcement of the strategic plan.

The result is that actions across teams and individuals are misaligned and the company is pulled in all directions.

For example, a payment solution provider’s competitive strategy may be to focus on providing payment systems for large hotel management businesses, offering industry-specific solutions.

If that strategy is ineffectively communicated and ill-enforced, teams may take actions and decisions that are counter-productive. Marketing may run campaigns that attract all hotel operators, large and small, to get as many leads as possible. On the other hand, customer success may adopt a low cost strategy to boost profit margin rather than offering enterprise level support for clients.

The result will be that marketing money is wasted on attracting the attention of small and medium hotel companies we don’t want. And down the line, customer success will have a hard time retaining large clients without proper resources to create deep relationships.

Misaligned goals across an organization will thus slow down the company’s growth, if not reverse it.

To avoid such a fate, it’s critical to first decide and agree on a competitive strategy among the senior leadership team. Each department head should have a clear idea of their role as part of the strategy and who they need to collaborate with. Afterward, leaders will need to design and communicate the strategic plan to all their team members.

Results from the company profile survey will reveal whether everyone understands the strategy. Should there be confusion, misalignment, or lack of information on what team members believe the company strategy to be, we’ll need to clarify the strategy (i.e. highlight decisions and initiatives that are aligned or misaligned), actively refuse resources to misaligned initiatives, and review team goals for strategic alignment.

With limited resource, there’s no time to waste on misaligned initiatives.

Following up on our example above, the payment solution provider’s marketing goal should be to attract as many large hotel operators as leads as possible, and to neglect any small and medium size operators. On the other hand, customer success needs to provide enterprise level support with an appropriate budget.

2- Is the company maturing as desired?


Keeping an eye on the company’s behavioral tendencies, strengths, and weaknesses helps leaders acknowledge the company position, and whether we need to change course to stay relevant.

As teams gain experience tackling their problem, and as new individuals join the team, a company’s strengths will evolve and new skills will be added. On the other hand, a larger team will also bring new organizational challenges (e.g. bureaucracy, processes, politics) that may add to the company’s weaknesses and frustrations. Externally, competition and changing customer expectations will often redefine whether a company trait has become a new strength or a new weakness.

Blockbuster‘s rise and fall is a great example of a company that failed to understand itself, and its position within a rapidly changing market. With the introduction of Netflix type services and changing customer expectations, Blockbuster’s competitive advantage evaporated. What were once strengths (e.g. a lot of physical stores and access to customers) became weaknesses (e.g. too much overhead cost), while existing weaknesses grew in impact (e.g. limited stock and selection). Should they have acknowledged these market changes early, there was certainly a chance to stay relevant.

Since a start-up’s operating environment can change month-to-month, it’s critical that we regularly evaluate its evolution and position within the market.

Are we too optimistic?


It takes a healthy dose of self-belief, courage, and optimism to found a start-up company. This positive outlook on the future is foundational to the culture of most start-up companies, shared by almost all team members that decide to join a start-up and forego a safe job.

I, for one, certainly believe in my company’s eventual success, even though we’ve yet to make $1 of profit.

Fact is, a positive mindset is necessary to pursue dreams and work on unproven solutions. If we had any doubt in our success, we wouldn’t be pursuing this venture. We know that the odds are stacked against us, and yet, we decide to put up a good fight.

The upside of having an optimistic mindset is clear: We always have the energy to get back up after experiencing failure, and keep moving forward.

Yet, there is also a danger to our optimism: It can make us blind to our weaknesses. At start-ups, we have a tendency to turn a blind eye to our company’s structural problems, strategic threats, and other long-term issues. These issues tend to be ones that we can’t solve right away and necessitate company-wide collaboration. And because there’s always more urgent short-term issues to solve at a start-up, we tend to ignore our long-term challenges. With time, the team learns to turn a blind eye to structural problems and let their optimism take over.

What’s the result? Blind optimism can cloud the evaluation of a company’s true situation. And slowly, it can become culturally unacceptable to voice negative thoughts. Team members may not raise or report their frustrations and challenges, for fear of being perceived as pessimists or even worse, not believing in the company’s future success. Complaints and frustrations will often follow with someone saying “Yeah, but we work with really smart people. We’ll figure it out.” Like that adds any value to the conversation…

The leadership team is certainly not immune to blind optimism (they need it most!), so they may become unreceptive to team members’ concerns, shielded by ego and by the fear that there’s nothing they can do about the issue.

At that point, the entire company is no longer capable of objectively assessing itself. Everyone drank the cool-aid. As it is no longer looking to improve itself, the company will slowly become unable to face changing market forces, to resolve internal challenges, and ultimately, to hit its goals.

So allow me to share a word of advice: When assessing the company’s profile, ask team members to be brutally honest. In the wise words of my yoga teacher: “Observe differences, don’t judge.”

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

What KPIs should my team use?

What KPIs should my team use?

I’ve heard this question asked a thousand times. The answer, of course, varies.

As explored in “Influencer,” metrics guide our team’s focus. It promotes specific actions. So to effect change, it’s critical to identify relevant metrics.

For most industries, there exist basic measurements that all players use for comparison. For example, the airline industry has Revenue Passenger Mile, the hotel industry has Revenue per Available Room, and any industry that sells products tracks Inventory Turnover. These metrics, while relevant to assess a company’s performance against competitors or an industry benchmark, may not be any useful in assessing a specific team’s performance.

The way we go about measuring the performance of our engineering, product, and marketing teams may vary from company to company, depending on the unique challenges faced.

At startups, the challenge of identifying relevant KPIs is intensified by rapidly shifting goals. Sometimes, a KPI is no longer relevant after just a few weeks. At our startup, we once changed the sales and implementation process three times over the course of a quarter, which necessitated three different sets of KPIs to be designed and adopted over the same amount of time. Chaotic, right?

So how do we go about defining a set of KPIs that focuses on long-term success, adapts to our changing team needs, and accurately reflects our progress? I’m going to argue that each team needs three sets of metrics:

  1. Strategic KPIs reflecting the team’s long-term mission, which shouldn’t change often;
  2. Tactical KPIs guiding the team’s immediate actions; and
  3. Individual KPIs guiding individual team members.

Let’s explore these three different types of team KPIs in more detail.

What pain does my team solve?

Ultimately, our team exists to solve a pain. The strategic KPI(s) that guides our team should therefore be a measure of how well we are solving that pain. So before thinking about measures, let’s first get an understanding of the problem our team tackles.

As an exercise, let’s assume that we lead a customer success team at a B2C retail company for a moment:

  • What pain does my customer success team solve? Bad customer experience.
  • How do bad customer experiences impact the company? Customers will not come back, and could also defame our brand on social media. In turn, they drive down future revenue.
  • What are indicators of bad experiences? We can learn about a bad experience when someone files a complaint, provides negative feedback, responds negatively to a survey, or speaks negatively of our product on social media.
  • What are indicators of repeat business? The lifetime revenue of our customers, the ratio of repeat customers, and the average time between purchases.
  • Can the metrics be used for comparison? Are some metrics parent to others, and can they be normalized?
    • All data points on bad experiences can feed into an overall count of negative experiences. We can further normalize by the count of active/purchasing customers over a time period, accounting only for customers that had the opportunity to have a negative experience. A relevant KPI could thus be the average count of negative experience per active customer by month.
    • The ratio of repeat customers and average time between purchases will both affect how the lifetime revenue of our customers grows. We can further cohort or group customers by their first purchase date to see if newer customers respond differently to our tactics. We can also take snapshots of customers’ lifetime revenue at different instances in their lifetime with us, to fairly compare new and old customers. For example, we could evaluate the lifetime revenue of customers that made a first purchase in the month of January, and their lifetime revenue 180 days after, and 365 days after…

As exposed above, we can clearly identify our team’s strategic KPIs by evaluating the context of the pain solved by our team, and by identifying parent metrics that others feed into. In this case, the customer success team’s strategic KPIs can track:

  1. The lifetime revenue growth of its customers by first purchase month cohorts; and
  2. The average count of negative experience per monthly active user.

How are we solving this pain?

To solve the pain that our team is responsible for, our team is likely to adopt different tactics over time. Each of these tactics also need to be measured and evaluated, leading to the need for Tactical KPI(s). Let’s again assume the leadership of our customer success team and explore some questions that can help us identify our tactical KPIs:

  • What is our team doing to boost customer lifetime revenue? We’re sending email newsletters to recommend specific products to a target audience.
    • How can we measure the newsletter’s success? By evaluating the number of repeat purchases that originate from our newsletter.
  • What is our team doing to reduce bad experiences? Solving problems to avoid a recurrence of the same problem with other users (i.e. fixing product issues and improving QA process)
    • How can we measure the success of our QA process? By counting the number of unique problems reported by customers for each product sold.

From the questions above, it’s clear that the customer success team’s tactical KPIs should track:

  1. The ratio of repeat purchases made by customers that clicked on the newsletter; and
  2. The average number of unique problems reported per product sold.

It’s important to note that a team should be able affect its tactical KPIs, and avoid metrics they can’t impact. In addition, as a team’s activities and methods of solving its pain evolve, the tactical KPIs should change. As a simple example, if our customer success team no longer send newsletters, and has moved on to using Facebook to interact with our customers, then we’ll need to track the ratio of purchases originating from Facebook.

How is each individual solving this pain?

Beyond team level metrics, there are also individual level metrics that assess how each team member is doing relative to another in helping to affect our strategic and tactical KPIs. The exact measure will depend on the team member’s unique responsibilities, and expectations that we have of them.

If two team members share the same responsibilities, the same KPI should be used for both of them. For example, sales agents that do the same thing should share KPI(s) to help compare their performance (e.g. Ratio of conversion from A to B).

A couple questions that can help us identify relevant individual KPIs include:

  • How does the team member contribute toward the tactical KPIs?
  • Are there unique expectations and improvement areas that we agreed upon with the team member that needs to be tracked?

Do individual KPIs have to relate to Strategic and Tactical KPIs?


Individual team members should never compare themselves and gauge their performance on anything else but what matters to the team and the company. Everything else is a distraction. If team members start comparing each other’s professional growth in terms of the quality and price of computers / desks they have, the clothes they wear, or their business card designs, then our company is doomed.

Does this mean that we shouldn’t seek to have fun at work? Of course not. Realize however that the goal of social events, company sports teams, and non-work related contests (e.g. Christmas prizes, best halloween costume, etc.) is to make the workplace and our culture more appealing to employees. Our hope is that people are more motivated to focus on their team KPIs if they enjoy working here. So it’s all related 🙂

What if another team shares my KPI?

Great! Sharing KPIs is great news, because 1) it shows that our organization is capable of strategic alignment across teams, and 2) we get to work with people that think differently than us!

There are a couple considerations to account for when sharing KPIs with other teams:

  1. Ensure that each team’s responsibilities are clearly defined; and
  2. Have someone from each team manage the collaboration.

It’s obvious that the first point ensures everyone knows what they’re supposed to do, and avoid stepping on each others’ toes.

It’s the second point that some organizations fail to foresee a need for. May it be a project or program, having a specific individual manage the collaboration ensures that there’s an advocate on each team that will coordinate work, provide detailed updates, and remind the rest of the team of this KPI’s priority. Without collaboration managers, shared KPIs won’t have the same priority across teams. This can result in missed expectations and conflict if one team tried really hard, while the other slacked.

Do I trust the data?

Beyond designing the relevant KPIs to effect the desired change, trust in the data is critical for team members to take the numbers seriously.

Luckily, there’s a simple way to verify whether our metric is accurate: Get a second opinion.

If we’re expecting something different, it means that we’re receiving redundant information from a different source that reveals a discrepancy. We must therefore compare results from the two sources, understand why there’s a discrepancy (definition, data, etc.) and either leave the two as is and acknowledge the difference, or change one of the two definitions to reconcile.

Where can we get a second opinion? If we’re asking this question, it must be that there’s no easy access to redundant information from a different source.

For example, while we may be able to compare revenue from our payment processing system against the data we see from our operational database, it’s not as easy to find a second metric to compare employee satisfaction scores from a recent survey. So what do we do? We walk around the office, observe people, listen to water-cooler conversations, and have lunch with colleagues.

I can’t overstate the importance of simply gathering qualitative data. Managers need to dedicate time weekly to observing their team, colleagues, and customers. We can’t be the ones that eat lunch at our desk. It’s incredible how much insight we can gather by simply observing our environment on top of looking at dashboards. I also can’t take credit for this: I was reminded to observe team members by my boss after failing to realize that some individuals were unhappy with their growth path. I didn’t need to wait for the next performance review or the next employee survey to get this insight. I could have simply invited team members for coffee regularly. Andy Grove (former CEO of Intel) is a strong proponent of this tactic as well in High Output Management.

Hope you found this valuable 🙂

Recommended exercise

Let’s review all data reports we look at weekly and ask ourselves: “Which reports did we skip over or simply glimpsed at?” These reports are often meaningless distractions and should be replaced. Reports need to be actionable, meaningful, and serve as a strategic KPI, tactical KPI, or individual KPI.

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

I disagree with my boss, what do I do?

I disagree with my boss, what do I do?

Every person working at a startup has an opinion on how to grow the company. This is largely because startups attract hungry people that want to have an impact, lead, and change the world. Not only that, these individuals want to do all this today. Not when they hit 40, or when they have a ton of experience in a particular field. Today. They want to affect change the moment they leave school.

I know, because I’m one of those individuals.

Since established companies have relatively successful processes and business models, not to mention experienced managers and leaders, it’s much more difficult to affect change at a young age working for them. So we take a shortcut: We join a startup.

However, if we believe that by joining a startup, we will always affect change the way we want it, then we’re setting ourselves for great disappointment. Startups, like any company, have obligations to its customers and its investors, which means that we have to do what is right for those individuals, not just us. And for individual contributors and middle level managers like us, we also have to get approval from our boss before taking big decisions.

So what happens when we disagree with our boss on a critical decision? What if we don’t like the responsibility that is assigned to us? What if we think the company strategy, or lack of, is unproductive?

We could leave the company and find something else, but there’s no guarantee that the same thing won’t happen elsewhere. We could also disregard their comment and simply do what we think is right, but that’s creating further conflicts.

Or we could recognize that our boss also wants what’s best for the company, and try talking out our differences. We could try to understand our manager’s perspective and reasoning behind the decision, and share our perspective as well. Why do I favor this option? Because we don’t know everything our managers do, and they don’t know everything that we do. I’m of the opinion that getting upset before we confirm all our assumptions is quite unfair. So let’s share our thoughts and try to get agreement.

Here’s a personal example:

In one case, I was really adamant about a direction that we could take with our product. Based on preliminary market research, we could gain some serious competitive advantage over our competitors with a new feature.

After speaking with my CEO about the idea, we both agreed that further research was warranted, but that there was a clear opportunity. So I led further market research. It was clear that I was passionate about the idea and wanted to lead the project.

Yet once we reached the planning stage and were ready to start work, the rug was pulled from under me and someone else was put in charge of the project, pushing me aside as an “advisor”. I was pissed.

So what did I do? I followed my personal rule of not reacting for 24hrs when I’m emotional, so I focused on other priorities for the day.

After a night’s sleep, I went directly to my CEO and asked for a 15min conversation to clear the air: I directly asked about why another individual was chosen instead of me to lead the project. After hearing my boss out, I gained some additional insight. We even came to an agreement.

Long story short, the project was given to someone on the product team because they are ultimately in charge of our product direction. It would be unfair for me to take over the job of a product manager when I’m not on their team. Fair point. On the other hand, I argued that I had the most knowledge about the project, in addition to having more experience with certain skills that the project requires. So after some exchanges, we came to an agreement that I’d sit on the project as a stakeholder, that all decisions will need my approval, and that I would participate in all product reviews. Yay!

That’s what I had wanted all along. I wouldn’t have minded project managing, but that wasn’t my priority. I was much more concerned about having a voice in how the new product feature gets built, and I got it. I learned about my boss’s perspective, shared my own, and we came to a new agreement. It felt great.

Now, things don’t always go smoothly. So what if I still don’t agree with the decision after talking?

Before quitting the company or going rogue, let’s ask ourselves one last question: Do I trust my manager as a leader, and believe that they have the right values and principles?

Fact is, even after speaking with our manager, there will still be information that we do not have. Our manager may be keeping some information confidential for legal reasons, may be protecting us from harmful knowledge, or simply understand the context of the situation better. So we need to take a judgement on whether we trust our manager as a leader, and whether we respect their character.

If we trust our manager, my opinion is to also trust them with this specific decision and tackle other priorities. As long as we share the same long-term strategic vision as our manager, let’s move on. And fact is, there are usually no clear right answer to a problem, just one that achieves the goal more effectively. So as long as our goals are the same, our manager’s choice still advances us towards the ultimate goal.

If we do not trust our manager as a leader, disagree with their values and principles, then it’s time to consider finding a new team. We simply don’t trust them to lead us anymore. And when we don’t respect our boss, we’re bound to have negative emotions at work and become unproductive. Life’s too short to be frustrated.

So let’s try to get on the same page and validate our assumptions before taking drastic actions.

Finally, HBR has a good article on how to prepare for the tough conversation once you’re ready to disagree. Enjoy.

Recommended exercise

Let’s ask ourselves: “Do I trust my boss?” If not, why? And have I been able to communicate that to them? Have I given them a chance?

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

How to approach tough conversations

How to approach tough conversations

We’ve all had tough conversations: Give negative feedback to a colleague, suggest a radical idea to our boss, or stand up against something wrong publicly.

These conversations are uncomfortable, because they have the potential to create conflict. In the worst case scenario, people will yell at us, react violently, or have us fired. So sometimes, not sharing our thoughts is the safer option.

No. Wrong. That’s not an option. Not at a startup.

In my opinion, not exposing what’s on our mind translates into not believing in our team’s ability to discuss bold ideas and receive critical feedback. As result, we stop seeing different perspectives and limit our ability to innovate. If we’re withholding a thought because we fear conflict, we might as well quit. It’s a sign that the workplace has a close-minded culture. Why would we waste our time at a startup where we cannot be honest with each other?

If we’re withholding a thought because we fear conflict, we might as well quit.

As leaders, it’s our duty to create a safe environment where team members can hold tough conversations with each other. Teams need to be able to disagree, to share constructive feedback, and to be honest without getting emotional.

To make tough conversations less uncomfortable, we need to focus on the issue rather the individual. The idea rather than the person behind the idea.

To this effect, allow me to share a three step approach that helps me approach tough conversations:

  1. Communicate the context of the conversation, along with supporting facts to our argument: Sharing why I’m talking ensures that the other party understands the context of the conversation. Next, I expose non-arguable facts and stats, which the other party cannot disagree with. The goal at this stage is to start from the same page.
  2. Reveal how we perceive or interpret the facts listed previously: I now reveal my opinion of the situation by sharing how I feel about the facts or stats exposed. To avoid debate, I state clearly that this is my personal opinion, and that I simply want the other party to acknowledge my perspective, not necessarily adopt it.
  3. Get onto the same page about the problem, and come to an agreement on how to resolve it: Finally, I open the conversation to the other party to see how they feel about the situation, and try to get onto the same page again by seeking their perspective. In other words, I’m validating my interpretations and assumptions. If I have an action item or takeaway for the other individual in mind, this is where I work with the other party to agree on it.

Let’s explore how to use this framework in real-life scenarios.

I. Giving constructive feedback to a colleague

One of the most common and uncomfortable situations we encounter at work is the urge to give feedback to a colleague. Maybe our colleague made a mistake, did something that we would never do, or even offended someone.

To avoid conflict, we have a tendency to not share our feedback. Yet it doesn’t have to be uncomfortable! Let’s think about the situation in a different light: The reason we want to share feedback is because we want the other individual to do better, to be more effective, or to learn something new. Guess what: They want the same thing!

So here’s how we apply our three step framework to help our colleagues grow:

  1. Describe the context and facts that support our argument: Hey, can I chat with you about increasing our team’s ratio of follow up sales calls? I noticed that you’re emailing prospects to schedule follow up calls.
  2. Reveal how we perceive or interpret the facts listed previously: In my personal experience, prospects take a long time to get back to me by email, if at all, so I simply schedule the follow up call while I still have the prospect on the phone.
  3. Get onto the same page about the problem: Do you have problems getting follow up calls scheduled via email as well? Have you tried scheduling it right on the call?

Let’s explore another case:

  1. Describe the context and facts that support our argument: I’d like to discuss how to make our meetings more productive. In the engineering review we just had, you raised your voice at John when opposing his idea on X. Here’s a recording of the conversation…
  2. Reveal how we perceive or interpret the facts listed previously: In my opinion, that was disrespectful to John and unprofessional. Even if you disagree with his idea, there is no need to raise your voice and intimidate him that way. It made everyone in the meeting, including myself, very uncomfortable.
  3. Get onto the same page about the problem: Do you recognize that it was disrespectful and unprofessional to raise your voice to someone? What do you think is a solution to this?

In the scenario above where the fact or event that we’re leveraging to illustrate our point is very specific, I recommend bringing it up as soon after the event occurred as possible (especially since we usually don’t have voice recordings of meetings). This avoids scenarios where the other party cannot remember details of the event. Often times, people are unaware of their bad habits.

II. Saying no to an idea

Rejecting someone can be difficult. It can destroy a person’s confidence, and cause the person to never bring up an idea again. So let’s explore how to say no with reason:

  1. Describe the context and facts that support our argument: I’d like to chat about how to best use our team’s resources and making sure we’re setup for success. First of all, thank you for bringing up the idea of hiring a consultant to help coach the sales team. Fact is, our current budget doesn’t allow us to hire such a consultant. Our budget is currently fully allocated toward salary, bonuses, sales software, and advertisements. It thus leaves no room for a consultant.
  2. Reveal how we perceive or interpret the facts listed previously: In my opinion, the team can improve their sales skills individually by reading about the Sandler system online and save money that way.
  3. Get onto the same page about the problem: Do you agree? What do you think?

Note how we didn’t give an absolute no. Instead, we explained why it is not possible to pursue a certain idea. We left the door open to explore alternatives and for the person to debate our opinion. It’s as desired to keep the door open to radical ideas.

Who knows… perhaps the team may choose to forfeit their bonus to get a sales coach instead. That’s fine by me. Or maybe I’m not aware of evidence showing that a sales coach has a higher ROI than ads, in which case it’s more logical to hire the sales coach and reduce our ads spend. Often times, explaining why we’re saying no will catalyze disruptive and innovative ideas. The one thing to avoid doing is saying no without reason – it communicates that we’re either close minded or don’t trust team members with our reasons.

III. Disagree on a decision with our boss

It can be most intimidating to disagree with our boss. That’s because we may create a conflict that we are unlikely to win. However, we don’t have to make it personal, and we can use the opportunity to try and understand whether there are other factors in a decision that we are not exposed to. So let’s give our boss the benefit of the doubt as they may have additional intel:

  1. Describe our expectation and facts that support our argument: Boss, I’d like to discuss how to best position our product for success in the upcoming quarter. Specifically, the decision that was made around building feature 1 rather than feature 2. Fact is, 60% of customers surveyed want feature 2 compared to 45% for feature 1. Feature 2 is also estimated to take half the time to complete relative to feature 1. Finally, the estimated yearly ROI of launching feature Y is 50% higher than that of feature 1.
  2. Reveal how we perceive or interpret the facts listed previously: In my opinion, to increase our revenue and achieve our growth targets, it is most beneficial to the company if we prioritized feature 2 instead of feature 1.
  3. Get onto the same page about the problem: Do you agree? Are there other stats or factors that I’m not aware of that led you to decide to focus on feature 1 instead?

This approach gives our boss a chance to be transparent and share why they think developing feature Y is more important, and for us to learn more about our boss.

Before I end this blog post, allow me to share a good HBR article on how to approach tough conversations, check it out here:

Recommended exercise

Let’s pick something that we’ve struggled to communicate to someone (boy are there many of those…) and practice communicating it with a trusted friend or colleague.

Are you leading a startup team? Get started on the right foot with the Start-up Manager Handbook. And subscribe on the right for new insights every week!

(Featured Photo © Jeff A. Goldberg)