Case study

Forks in the road

October 12, 2021


5 min read

Simeon Wishlade
Simeon Wishlade
Principal Product Designer
Forks in the road

Careers aren’t like following directions In Google Maps – I can’t put in ‘CEO’ as a destination and follow the blue line until I reach that role. There are twists and turns, ups and downs and in some cases you might look back and wonder if you’re heading in the right direction. In this article I’d like to share my experiences of taking leaps into new roles, sometimes discovering that they’re not for me. What follows are some things I’ve learned and how I approach new opportunities.

Career paths at OpenTable

As a designer at OpenTable we have an established career ladder to evaluate how we’re progressing in our careers. Our entry level role is a Product Designer, and from there it progresses to Senior, Lead, Principal and Senior Principal. We have plenty of opportunities to follow other paths too, we’ve had people move from Product Design to Research to Product Management, or, like me, have moved from Product Design to Product Management to Product Design, to Design Manager and back to Product Design again, (while in between dabbling with FE engineering). Career paths are fluid and we find that we’re drawn to and would like to try an alternative discipline we’re supported and encouraged to do so. we’re supported in what we want to achieve. 

Design Management

When you’re the most seasoned and senior designer on a team, you might be asked the question: ‘Would you like to be a Design Manager?’ 

I have watched two fellow designers move into management – they were brilliant designers, and they both made awesome managers. I watched them get invited to leadership meetings and offsites, and grow their influence by growing their team. I don’t know when it happened, exactly, but I started to think that you had to be a manager to have a great design career. 

Some designers know they want to manage – but I was not so sure.  When I was offered the position of design manager I was flattered, but I didn’t think I was management material. I kept asking myself:

  1. What if I fail? What if I am a poor manager? What if I fail my team?
  2. Why have I spent so many years becoming good at my craft only to step away from it?

If you’re unsure about management, you might have the same questions, and others too. I've seen unsuccessful managers who let down their team. Who would want to be in that position? But, it’s also worth thinking about the questions inversely:

  1. What if I'm successful as a manager?
  2. What if the team really responds to me? 
  3. What won’t I miss now that I’m not doing design work?
  4. How would I feel if I can get my reports to grow and develop and help them get promoted in their career?

And if you can think about the questions in that way, maybe you’ll be able to decide on whether that helps you make that decision. For me these questions helped me to make the decision to accept the role. I took on the management of designers, hired designers for my team, helped make decisions that affected our broader design team, and grew in ways I wouldn’t have solely as a designer. 

I loved many aspects of being a Design Manager, but I really missed solving product problems, I missed testing solutions, speaking with users, discovering something I didn’t know. And so after 18 months I moved out of Management and back into the role as a Product Designer.

Before I took the role of Design Manager I might have considered this move a failure. But I have in no way failed. I have learnt so much from taking a step way outside of my comfort zone and out of a role I’ve been doing since leaving university that I have grown in ways I would never have before.

And so I share some learnings from taking steps into the unknown and why you should grab the opportunity by the horns and give it a go.

It’s not failing to say that you don’t enjoy the new role 

It might feel hard to say that the role you accepted isn’t for you, but not everything has to be. You might well be good at it, but it just doesn’t bring you any pleasure. As long as you can walk away from the role having learned something from it, given it your all, that’s all that’s expected of you. 

If you accept a role, define your goals and what success looks like over the next six months to a year, and keep track of how you feel. You might also want to define what failing looks like to help guide you. Understanding what failure looks like is as great as understanding what success looks like. 

Having more empathy for those your work with

One of the benefits of moving in between roles is having more empathy with your partners.

Having worked as a PM I understand that there are many moving parts, requests, and strategic changes that affect even the best of quarterly plans and disrupt what you’re doing (which is why we might do design work that never gets built).

Having spent time with engineers and coding my own tests I understand the process in which we go through to publish something to our site, who needs to review it, whether it breaks anything, passes tests, whether there’s conflict with code being written by someone else – who merges first. But also how incidents, requests from other teams, and priorities within the company can sometimes push the engineering work that you’ve done the designs for down the list and how sometimes not built at all.

And having worked as manager, I have more empathy for my manager. Because I can understand the work that she does on a daily basis I can try to support her in the best way I can, taking care of smaller tasks so she doesn’t have to think about them, helping in the recruitment process, and helping think about processes within the team and how we can be more visible or effective.

Leadership skills

Being put into positions of leadership might fill you with fear (it did to me), but having been in them now, I’m certainly more comfortable leading, managing issues and making decisions. This might boil down to leading team meetings, leading an initiative, putting your hand up to help out with organising events within the company etc. You don’t need to be a design manager to lead, you can lead by mentoring as an IC, having 1:1s with your team to talk about work and progress, by looking at processes, by helping make strategic decisions around projects by less senior members of the team, by writing articles, by speaking at conferences, and so much more.

Better relationships with others

As a manager you’re likely to be liaising with a wider network of people within the organisation, from Engineering leads, PMs, Sales, C-Suite etc, and working out how to make the design team more effective. This doesn’t mean being quicker in turning around designs, but it does mean understanding how we are perceived by others in the business and what we can do to improve the relationship between the design team and the company.

You don’t have to be a manager to do this. Asking questions like ‘How can we be better as a design team? ’How can we communicate more clearly?’ ‘How can we expose people to our work should they want to see it?’ can be asked to anyone, by anyone. It makes you a point person to help drive these changes.

Knowing more about yourself

For me, being a manager for 18 months really helped me focus on areas that I wasn’t confident in. It’s helped me be the centre of attention, and be a leader. It’s helped me think about the team, who might we want to hire, and what skills we are looking for, and about being proactive in helping out others. It’s made me more well-rounded and equipped to support the company. I’m happy to put my hand up and help out with tasks that in the past I would have shied away from, or be a part of organising an event for the team that I previously wold have avoided at all costs. 

And you can grow in other ways too...

Regardless of what you think, I would encourage you to take on the role, discuss with your manager what success would look like in six months / a year so that you can have the conversation about whether you think this is for you or not. The best thing to happen is that you discover that you love a change in role. The other best thing that could happen is you realise that you love the role you’re in already.

And going back to the analogy about Maps - entering a destination often gives you a few different ways of getting their. Taking Route A might be the quickest, while Route B & C are more scenic and you’ll end up driving through places you’ve not been to before. Who's to say that on these alternative routes you could discover a place to stop, find a good coffee shop, have lunch and discover you’d like to spend time here rather than go to your original destination.


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Simeon Wishlade (he/him/his)
Principal Product Designer

Sim helps create tools for restaurants to showcase themselves, and how diners can view and interact with this content. He’s based in London, loves food, loves running, loves solving problems.