This article is written by Amanda Schwartz Ramirez, who is a COO advisor for emerging tech startups and previously spent a decade at PayPal as a strategy and BizOps leader. She digs into the challenges of running operating practices at startups in her newsletter, Thinking in Quarters.
There’s a distinct feeling I’ve had in leadership meetings – a pounding in my chest – whether it’s a large in-person meeting, or staring at a dozen faces on a Zoom screen. It typically arises not as a response to what is being shared in the meeting, but from what I’m not saying.
Because, instead of taking the leap and bringing up that concern about our launch plan (and risk upsetting Jon, who has been working nights and weekends on this), or surfacing that unaddressed risk in our financial model (and rabbit-holing the discussion for 20 minutes), I decide to just not go there. Maybe the issue will resolve itself naturally.
It’s a feeling that I now can identify as fear – and looking around, I can’t help but wonder who else in the room might be feeling the same way.
The problem is, going there is exactly what makes these operating exercises valuable.
Rather than focusing on day-to-day execution, something most startups excel at, strong operating practices (like goal-setting, planning and business reviews) require something different. Teams must use a wider lens (much wider than the one they look through every day), deeply consider future states (possibly distinct from the one they are currently chasing), and agree on a concrete course forward (one rife with unknown-unknowns).
This requires that teams put all of their cards on the table, and enter a space of reflection versus reaction. That they express the underlying concern that is preventing them from buying in completely. That they sidestep fear, for even just a moment, in order to envision what could be true.
Slowing down to go fast
Now, before you start grumbling about how you don’t have time for this – you’re running a startup! You need your teams to just “move fast, break things!” (or insert your favorite mantra here) – please, hear me out.
Behind these pithy slogans tends to be a dangerous assumption that everyone is on the same page – that they know what to move with urgency towards, and what can break; that they know how the company is performing, and that they are interpreting and processing the events of the market in a similar fashion.
But I’ve found that in most teams, especially those operating in complex environments while rapidly shipping, this is simply not the case.
And this problem compounds as teams start to scale. In fact, I regularly observe teams grow from 10 to 25 and completely lose the thread on what they are there to achieve. During times of change, execution is no longer about staying heads-down and building – instead, it becomes about:
- Staying grounded on a thesis and figuring out how to get smarter over time as a team.
- Saying “no” to countless distractions and focusing on making the right few bets.
- Bringing in and properly utilizing new skill sets to expand the team's capabilities over time.
The above requires intentionality and real alignment on what you are going after, and what really matters along the way. To achieve this, as a leader, you need to acknowledge and help mitigate fear.
In this piece, I’ll cover a few common fears that plague all of us in the workplace, particularly around goal-setting, and I’d like to offer a few tactics for keeping them at bay.
In most organizations, goal-setting tends to be a time when hopes and fears are translated onto a page.
These lessons were born from patterns that I started to recognize during nearly a decade leading dozens of leadership teams at PayPal, and now as a COO advisor to early-stage startups.
Whether you’re considering H2 planning, or just navigating the difficult terrain of today’s market, I hope you pick up some practices that you can apply to help keep your teams aligned, grounded, and operating with less fear.
5 COMMON FEARS (AND HOW TO KEEP THEM AT BAY)
So, let’s dig right in and go through a few scenarios that tend to undermine the very collaboration needed to get the most out of your operating practice (along with some fictional archetypes to help bring each to life).
THE FEAR OF FAILURE
Julia is a seasoned SVP who refuses to set an aggressive target for her team. She’s learned from previous roles that if she sets a target and misses, it’s likely that her budget will be cut next year. So instead of buying in and going big, Julia goes for a modest target that she knows her team will over-perform against.
Tyra is gun-shy to agree to a target, and she’s gone silent on the email thread. Why? Because the last time she went “big” and failed, she felt like she lost vital ground with her peers and her CEO. The culture claimed to believe in “fail fast” – until Tyra did.
Golden Rule #1: Set the tone.
As a startup executive, you are leading everyone through a grand expedition — what you're attempting has never been done before, and it's going to require that you utilize every ounce of skill and resources that you and your team have at their disposal.
But at a fast-growing company, it's very easy to become hyper-focused on your piece of the puzzle, rather than how the constellation of pieces fit together. This is why team-building exercises, like ropes courses and escape rooms, are a favorite on leadership team offsite agendas: to remind you that you’ll accomplish much more together, versus going about it alone.
The act of “team-ing” is a muscle – and if not exercised, it will atrophy.
So, at the start of a goal-setting exercise, or better yet, throughout the quarter – remind your leadership team that they are, in fact, one team. Reinforce the expectation that everyone works together to reach the summit. Also, state the rules of the game. Some tactical tips include:
- Build in trust-building: Make sure there is an opportunity for relationship-building before the process truly kicks off. This can be part of an offsite, a thoughtful dinner and activity, or something more creative. The point is to make sure it happens, and that it builds some connectivity across the team.
- Clarify the purpose of goals: Too often, goals are viewed only as a tool for accountability, and in that light, they become punitive. For example, it’s common in more scaled companies for achieved goals to translate to bonuses or increased budgets, while missed goals lead to more rigorous reviews or cutbacks. Ensure your team is clear on your intent before you get started. In early-stage startups, couch goals as a tool for collective learning, transparency and synchronization across teams.
- Get specific on definitions: Most execs come into goal-setting with their own assumptions (and baggage). You can speak to four different leaders and you might get four different philosophies regarding what it means to achieve a goal. For example: 1). All goals need some margin for error (success = 70%). 2). Goals and plans are interchangeable – you either achieve, or you don’t (100% or bust). 3). Shoot for the moon! Land amongst the stars! (50% is a massive success). 4). Set modest targets and wildly outperform (150% is celebrated). There’s no one right answer — what matters most here is consistency. Pick one definition of success and ensure everyone knows it.
THE FEAR OF LOSING CONTROL
Jay is a talented product leader who can’t seem to find the time to discuss his goals with other departments. When asked to upload their goals and seek asynchronous input, Jay still won’t play ball. Turns out it’s less about time and more about buy-in – product has their roadmap, what is the point of meeting for input on it?
Rita knows, as CEO, that it’s her job to rally her team with clarity and conviction. What better way to do it then to set a north star and move everyone towards it? But what if the north star turns out to be south, and she needs to change course? What if the team gets too committed to the wrong direction and Rita cannot pivot everyone fast enough around what’s right for the business?
Golden Rule #2: Create some structure
Structure may not seem like a very appealing word — particularly for a fast-moving startup. But allow me a quick aside to point to an interesting insight a wedding planner once shared with me: the majority of folks do not like open seating at weddings.
At face value, you might assume (as I did) that giving everyone the freedom to sit where they’d like, rather than assigning tables, will create a more relaxed atmosphere. It turns out the opposite is true – it creates anxiety. Over countless weddings, this wedding planner observed guests racing from the ceremony to the reception to find friends, count available seats, rush through the necessary “hellos” before claiming their spots with their purses and jackets. All of a sudden, this supposed low-key wedding atmosphere becomes a mad dash of folks trying to find their place.
The same insight applies to goal-setting – but in this process, the stakes are higher. Instead of being stuck at the table with the groom’s college roommate and old next-door neighbor, you might get saddled with a goal that you need to rally your teams around for multiple quarters – one that you yourself do not believe in.
So, view structure as your friend, not your foe. Here’s how
Take turns
It’s common to see a leadership team come together, set a bunch of company-wide goals, and then distribute them with a deadline (“set your team goals by Friday!”) – this is the equivalent of open-seating at a wedding.
Instead, consider sequencing your asks for input and allowing teams to transparently take turns. The general sequence is:
- Step 1: Start with company-level North Star metrics: revenue, customer growth, etc – these tie directly to your company strategy
- Step 2: Set goals for each of the products, businesses, initiatives that move the company-level goals forward.
- Step 3: Taking the above into consideration, set goals for everything else (non-growth areas, functions, etc). These directly support everything above, and include other responsibilities for running the business (payroll, accounting, legal, security).
Between each step above is an opportunity for visibility, discussion, and vital feedback loops. With every turn, your goals get better and more aligned. This can still be done efficiently! In fact, with some structure, I’ve found that there is less rework down the road and more buy-in overall. Try accomplishing steps one and two at a leadership offsite.
Document cross-team handshakes
As a part of facilitating the goals listed above, host targeted goal reviews. Doing this will help you identify and broker critical cross-team handshakes. A skilled COO or ops lead is invaluable here for providing support in facilitating and capturing outcomes.
Here are three examples to bring this to life:
- Your product objectives likely depend on world-class marketing support. Host a session (or two!) where both Product and Marketing review and align on goals.
- Your organization intends to scale up and fast. Host a session with your recruiting lead to ensure they are accounting for your hiring needs in their plan.
- Sales needs faster turnaround on contracts in order to hit their goal. This requires more thoughtful engagement across your sales, finance and legal leads. Host a session to really nail down swim lanes (or who does what and when) between these teams.
This is not about boiling the ocean – it’s about creating space for quality conversations that lead to agreements between teams to support one another’s efforts.
Set up a monthly review
In a recurring structured meeting, review progress against your goals and discuss learnings along the way. The frequency here is less important than the practice – for some startups, quarterly is far too long to go without talking about the goals versus reality; for others, it’s just enough time to make progress before reconvening.
The point is to ensure your team knows that you will convene regularly to review goals and learn together. Over time, this will give your team a place to bring their bigger questions (“Are we doing enough on marketing?” “What about this new idea?”) and a forum for addressing their underlying concerns. This prevents fear from bubbling for too long.
THE FEAR OF CONFLICT
Jordan knows how she feels about her go-to-market strategy, but she also knows that it’s the polar opposite of how James feels. Maybe she’s the only one who feels strongly, and she might not be up for that fight. Especially now, when she and James are finally working well together after some initial friction.
Sean is new, and sure, he was hired to “lead design” but Design still reports into Product. He’s still getting to know Jay, the Head of Product, and doesn’t want to step on any toes. He might just hang back and wait for Jay to ask Sean for his input.
Golden Rule #3: Settle all turf wars
A very real and consistent source of heartburn during goals conversations, especially for dynamic organizations like startups, is an underlying question of who’s responsible.
We’ve all seen these points of friction crop up:
- A new leader is transitioning in, or an existing leader is transitioning out
- A business line is run by product, sales and marketing
- A function is established, but nobody knows what they really do
Before endeavoring to set goals, survey your leadership team and look for areas of ambiguity or conflict. You may not be able to resolve these completely, but aim for achieving clarity on who gets to make decisions about what each team prioritizes and ultimately works on. Here’s how:
- Formally welcome any new leaders that are joining or have recently joined. Aim to get any new executives on their feet before the goal-setting process kicks off, and help to ensure that they and the leadership team are clear on how your new executives will engage during goal-setting. It’s a wasted opportunity to have your new executive on the sidelines – loop them in intentionally and use this exercise as an opportunity for them to add value.
- Rip off the bandaid for org changes. If you have any upcoming org changes that you’re planning to make (shifting one team into another, moving operating responsibilities from one exec to another) – be decisive about whether you’ll do it now, or after the goal-setting cycle is complete. You’ll be deciding between possible pain today (change), and pain tomorrow (churn) – but the point is to make the decision. Don’t auto-pilot into the process and hope for the best.
- Be explicit with decision rights. Do you have a leader that is transitioning out mid-quarter, and is probably best suited to advise versus decide? Do you have an area of responsibility that is currently shared amongst 2-3 executives, and you want one to be truly on the hook? Do you have an area of responsibility that the CEO would like to delegate going forward? Have these conversations now – both with the leaders impacted, and the entire leadership team. Create clarity (even if temporary in nature) to minimize churn.
THE FEAR OF LOSING CREDIBILITY
Tom has been around for a while and is generally well-regarded for running a tight ship. But over the past few companywide AMA’s, Tom’s team has asked some pretty meaty questions of the leadership team – namely, what is the strategy, and why did we decide to pursue it? Turns out, Tom hasn’t really taken his team through the strategy document that was sent out alongside the goals. How could he? He didn’t play a role in developing it.
Satish is new to the company. When discussing strategy and goals, Satish gets pretty quiet, even though he has fundamental questions about what the company is doing and why. He’d rather put his questions (and valuable input) aside for now – better than looking like the clueless one in the room.
Golden Rule #4: Create a level-playing field
Remember that everyone is coming into the room with their own view of the world and their own opinion on your company’s approach. Goal-setting is the perfect time to converge on a shared view and make sure the team is truly headed in the same direction.
But how do you really do that — especially with new leaders, existing team members, and the noise of today’s market?
Reground your team on your founding thesis. Cut through the noise and help create a level playing field by documenting your thinking to date and hosting intentional discussions to ensure the team understands (and has space to question) past decisions.
Here are a set of question prompts to help get you started (and jot down your answers using this template).
- When we founded this company, what opportunity did we see, and why did we believe this company needed to exist?
- What have we learned since then about our customer, our offering, and our opportunity?
- Today, what do we believe is most valuable about what we are building, both to our customer and to our company? Be specific.
- What are 2-3 things we absolutely must nail in order to create this value? What must be true in order for this to work?
The questions are deceptively simple, but once answered, you’ll have an accurate articulation of the founders’ thinking and the current leadership’s perspective.
Once this is done, set up a couple of Q&As with your leadership team and set the stage for a “beginner’s mindset” conversation. That way, everyone comes in ready to ask questions and nobody is faced with the fear of looking dumb. Come out of this session with a revamped version of the document that can be shared alongside goals and plans. Some tips:
- Clean up and publish your founders’ thesis companywide. Update it quarterly and host AMA sessions companywide to ground your entire team on the big picture. Use this for onboarding at all levels.
- Refresh this document quarterly and use the redrafting and review process as a way to onboard new executives.
THE FEAR OF MISSING SOMETHING
Kristina is a member of the founding team and she’s got a ton of institutional knowledge to share, but isn’t quite sure how to do that most effectively. During goals conversations, Kristina has a tendency to derail discussions by dragging the group through all of the reasons why a thing didn’t work two years ago. While interesting (and important as backdrop), it’s really taking the air out of the room.
Gerard knows that we need to talk about our ecosystem development strategy. It’s been eating at him that we still don’t have one – we’ve been talking about needing one for months! So, when goal-setting comes up, Gerard finds an opportunity to broach the subject again. Maybe this time, it will get done?
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Golden Rule #5: Address your elephants
We all know about the handful of topics that tend to derail our planning discussions – you know, the elephants in the room.
Instead of allowing these to simmer below the surface, spend some time upfront deciding which of these you’re willing to explore now, and which you’re going to punt on for the time being. Be clear with your team beforehand – write these down and share them alongside any company goals.
For example, “I know we still do not have a mobile strategy. We are de-prioritizing that right now for these reasons.” Or “I know we still need to hire our Chief Product Officer. We believe that we can make meaningful progress on these things while we continue to find the right person.” Or “Yes, we failed when we launched that thing. We want to do better on XYZ, so let’s bring those lessons into these goals.”
If derailments persist, I suggest a few tactical tips.
- Pre-Meetings where you address your elephants. Sit with the members of your team who might have particularly strong feelings about the elephant that you’ll be addressing, and have a pre-discussion. Most tricky topics are easier to approach without the sting of surprise, so take that element out of the equation.
- Pre-Meeting with the “been there done that” folks. Sit with the few members of the team who have a high degree of institutional knowledge to share. Are there aspects of the goals or priorities that you’d like them to weigh in on? Are there pieces of history or knowledge that would be helpful to document before attempting to socialize goals with the rest of the team? If so, do that in advance.
- Document, document, document. Invest the time (grab support from an ops person!) in documenting institutional knowledge that tends to stay captured in the minds of a few long-time employees. While this feels like an immense amount of upfront effort to do, it relieves them of the burden of being the sole source of knowledge going forward. This may help them engage more meaningfully in go-forward plans.
Fear isn’t going anywhere in the workplace. No matter what your role, your tenure, or your company – it’s bound to crop up. But by trying a few tactics, leaders can stem the flood of fear that often comes trickling into an org and slowly derails it. Empathize with your teams – because you’ve been there – by removing fear-generating obstacles, and you’ll be more likely to create an environment that is more conducive to collaboration, alignment and at the end of the day, success.