Silvia Oviedo López has been at the forefront of scaling teams and shaping culture at both Canva and Pinterest. She unpacks why startups should take an iterative approach to org design - and provides tactical advice on how to do that without disrupting day-to-day operations.
For Oviedo López, a successful org design is one that doesn’t take itself too seriously. In fact, she argues that founders who are really invested in growth should treat org design like a hypothesis that can be tested, reformulated, and tested again.
At first glance, it’s antithetical to how most businesses think about the org chart. Generally, it’s either seen as a stale obligation, or the team finds it so boring they tend not to build it with any intentionality. By making it explicitly mutable the org chart can become something people want to engage and experiment with.
She argues that a hypothesis-based approach shifts focus from generic team structures to organising around specific issues that need to be solved. To illustrate, she uses play as an analogy: “Go back to being 10 years old, and think about playing with your friends. It's very different if you decide to play a game of soccer versus if you're going to play house. In both cases, everyone has to take on different roles. For soccer, you need a goalie, a forward, a referee. To play house, one person might be the parent, or the kid, or the neighbour.”
But, she explains, both games can’t be played at the same time. This is the critical point: “You have to structure the organisation so that it works well for the outcome you want to drive… in other words, for the game you want to play. It’s the same for the people you bring on board - if you're playing soccer, but the people you’ve chosen to play with think they’re going to play house, no one is going to score any goals.”
Having recently founded Blomma, an AI career coach, designed to give everyday professionals access to personalised, executive-level guidance, Oviedo López is right in the middle of applying her own philosophy at the early stage of a startup.
Why startups need iterative org charts
Anticipating change grants organisations permission to operate with greater curiosity and flexibility from the get go. Instead of building teams around generic functions, Oviedo López recommends an iterative approach that accounts for the reality of shifting priorities within an organisation.
“There are so many variables when you are figuring out whether you have the right organisation for the problem you’re trying to solve - and the right organisation for the outcome you want to drive,” she says.
The Covid-19 pandemic offers a recent example of a moment when everybody was proven very wrong at scale (something that doesn’t happen very often): “If you rewind back to December 2019, most companies had their yearly plans locked for 2020 - including leadership changes and succession planning. By the end of March, everyone was scrambling because the strategy they had was no longer valid. The macro conditions changed entirely, and the organisation they had - the leaders they brought in, the structure they put in place - wasn't working anymore.”
In periods of stability, organisations need leaders who are good at operating and making the most of the structures already in place. During the pandemic, a different kind of leader was called for: “Suddenly, the right leader was a ‘wartime CEO’ - someone who is extremely dynamic, able to respond quickly, and ideate against unpredictable conditions.”
“It was really interesting to see that at scale, where you had everyone going through reorgs one after the other, because nobody was getting it right. It was extremely hard to anticipate the next turn.”
The pandemic underscored the fact that businesses - especially startups - are always operating with incomplete information. Malleable structures therefore accommodate unanticipated impact better than rigid ones. “You understand the past, but you can only predict the future with your best guess. You don't control the macro conditions; you don't control what's going to happen tomorrow.”
“So, if you treat organisational structure as a hypothesis that you're proving or disproving - suddenly you have the space to make changes, adjustments, and optimisations based on the conditions you find.”
Organise people against problems
Rather than organising teams in a hierarchy, Oviedo López recommends organising them against specific, current problems that need to be solved. This helps to instil dynamism as a default at the organisational layer.
“Organisations tend to traditionally be thought of as hierarchies, which comes from the military. You have the CEO, then the C-level, then the directors, and however many people in your unit. Whereas in tech, we tend to organise a lot against problems.”
Practically, this looks like pulling in people from wherever they may be technically situated within the organisation, and placing them on teams that have a specific issue to solve.
“Functionally, they might report somewhere else, but if you keep a flexible org chart, you can aggregate the right people against a problem for a period of time. You define the problem, identify the people you need to solve it, bring those people together, solve the problem - and then shrink that team back to whatever you need for maintenance.”
Back to the play analogy: “For a game of soccer, you need 11 people. When the game is done, they can leave, and you just need one person to carry the ball and put it back where it belongs. Then, you move on to play something else.”
Hire people who can handle change
When Oviedo López is hiring, she looks for people who'll be flexible enough with the fact that their job is going to change in two years.
“At Blomma, for example, we're making decisions about the people we need to launch a company, those who can help to build a product, build an MVP, launch it, and grow it. Those are the things that matter most right now.”
She has gone into this period of Blomma with a hypothesis about the roles and skillsets needed, “but I hold it lightly and with the willingness to make changes in response to what happens in real time,” she says.
She breaks down how to find the right people for a dynamic organisation:
- Understand the conditions for success: “There are people who thrive in more dynamic environments and people who thrive in more static ones. You can hire a dynamic person into a static environment and have them be an agent of change and it can work really well - it just needs to be intentional.”
- Look for people who work well with unknowns: “Early stage startups need people who index very high on the ability to pay attention to what's happening, make a decision on what to do next, and then implement without hesitation. You also want people who exercise curiosity like a muscle - because they’ll be the ones who continually ask questions against the hypothesis.”
- Not every hire needs to be full-time: An org chart that is treated as a hypothesis requires flexibility to allow for adjustments and updates. “Start with part-time employees and transition to full-time when you need to - especially in the early stages,” Oviedo López says. This allows you to make hiring decisions based on which roles are actually giving you more leverage.
- Let the team in on the experiment: “You want to be transparent about what people can expect - so they aren’t surprised when it comes time for the change you already know is going to happen. Otherwise, you’re setting both them and yourself up for failure.”
Founder hiring hack: The one interview question Oviedo López always asks
“The one question I use to identify people who will thrive in a dynamic environment like this: Tell me about what makes a great day for you at work,” Oviedo López says.
It's a casual, conversational question that feels very innocent, but it provides deep insight about the ideal conditions in which someone will thrive. “People who like that fast-paced, chaotic environment will tell you: I love when I can context-switch and solve many problems. And on the flip side, you have people for whom a good day is: No one interrupted me. Nothing unexpected happened.”
Understanding what the conditions for success are lets a founder bias toward the right people for the game they’re playing.
When to proactively reorg
How often a business needs to actively reorg depends on the organisation, the culture, the people, the strategy, and the macro conditions, says Oviedo López. “What I've found is that if you treat it like a modelling or sculpting project - you're always chipping away, always adjusting - it feels less abrupt than when you come in with a clean slate.”
In other words, a slow and steady culture of constant optimisation is less disruptive to the organisation than scheduling huge overhauls at regular intervals. “It needs to be fluid and responsive,” she says.
The other key consideration is how org changes affect the people in the organisation, because people tend to become attached to their roles - either the one they were hired into, or the one they want.
“That's where ego comes in; we equate our worth to our roles and it becomes difficult to detach from that. You almost need to remind people that, at the end of the day, the jobs we have are made up. Your job description is just a collection of tasks that someone put together - probably using ChatGPT if we’re being honest.”
“The fix is to proactively give people agency to address real problems - not just to do the list of things given to them on their first day. You need to make change a normal part of the job. This also helps to create longevity when the role is constantly changing.”
To judge when things need adjusting, Oviedo López pulls one specific tactical lever at the manager-to-team relationship level. On whatever cadence makes sense for the business - “quarterly is a good one,” she says - have an honest conversation about where the team is spending their time and make a call about the following:
- What should you stop doing?
- What should you keep doing?
- What should you start doing?
Figuring out when things need to change comes down to having hygiene around focus, she says. “There are so many things we do just because we’ve always done them - but the business doesn't necessarily need you to do that anymore. I don’t think organisations are having these conversations enough, so teams end up repeating the same task list, even once the issue has already been solved.”
Let people know that change is coming, and it isn’t scary
In closing, Oviedo López reiterates that organising against problems is only an effective strategy when an appetite for and acceptance of change is entrenched in the culture of the business. Getting everyone in the organisation to value the method of testing and adjusting based on results goes much further than surprising people with change.
“Sometimes we think about what makes a team successful in such complex ways, when really it comes down to: what are the conditions in which you do your best work? And as a leader, how can you create the conditions that make the highest number of people thrive toward the objective you have?”
