First On: People with Danielle Silvestro

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Today’s guest holds a special place in the First On lineup. In addition to being a People expert and good friend she is also a former colleague of mine. Danielle Silvestro is the Head of People at Entrepreneur First, an early stage talent investment programme, and leads the company’s People function across its six global sites. Leading the internal talent department for a company that’s literally built to nurture great talent is no easy task. But in for 2 years I worked alongside Danielle and I can personally attest to her ability, empathy and extreme patience (which I tested more than once). Danielle brings a level of passion to the People function that any founder would be lucky to have. Her command of policy and best practice is matched only by her unwavering values and genuine desire to develop others. In our conversation we cover the thorniest People issues that every founder will face: compensating staff, growing a management layer, building a culture, etc.. We also discuss the change that the field has experienced over the past few years and what building a career in People means today. Please enjoy!

To start I’d like to ask for a walk through of your career within people and culture. 

My first job out of uni was within the civil service. When I took the role I didn't have a clear idea of what I wanted to do in my career, but I quickly found myself very at home in the HR world. When I joined we still called ourselves the “personnel department”, which shows how long I've been in HR and how far we have come. 

I feel really lucky that I started out in the civil service. Working for such a large organization was the perfect training ground to deeply understand how you can provide services at scale. We had over 2,000 employees distributed across Scotland, so it proved to be a good place to learn how to provide services to distributed locations from a central base. 

I then moved to London keen to specialize more deeply in an area I developed a particular interest in, reward. I joined EDF trading, which allowed me to learn from some very exceptional mentors who had really deep experience in reward. I think that specialized role has really paid dividends for me because pay and reward can be one of the more complex areas of people operations.

Then I made a somewhat surprising move. At the time I was really enamored by Byron. I loved the experience of going into the restaurants, where you could sense the team loved what they were doing. The people-first philosophy really spoke to me so when the opportunity came to join the team, I couldn't say no. At Byron I got very deep into employee engagement, which is one of the more energizing areas of People Ops for me. This also gave me the opportunity to experience very rapid scale. We were growing fast, at times a restaurant a week, with new teams of up to 30 people. This was a great experience for creating scalable processes that didn't break with volume. Then I went to KellyDeli, which was a distributed company with multiple growing locations in Europe. I love working in global HR, understanding the nuances and learning from different cultures. 

Then the opportunity came to join EF to set up the People function. EF has the strongest mission of any company I've worked with and I was very bought into this from the beginning. Over my career to this point, I'd been a key member of scaling and distributed people teams but setting up a people function from scratch was a new challenge for me. When I joined we were 50 people in London and Singapore only. Within my first month we started to scale and in that first year we expanded to four new sites. The EF team that I work with are really inspiring humans and have given me the opportunity to navigate through so many interesting challenges and learnings over the last 3.5 years. 


There does seem to be a shift away from the old “Personnel” function. I think of Toby Flenderson with loads of policy and a somewhat hated department. Now there’s “People and Talent”, which is very respected. Do you have any hypothesis as to why that shift has happened?

That is like trying to be friends with an evil snail! (this is my favorite ever line from The Office...)

In a people-first business, your team is your greatest asset. You need to think holistically about how individuals experience their journey as part of your company. The shift centers around being much more thoughtful and intentional about designing an employee experience that allows for people to succeed in their roles, leading to happy and productive teams. 

We all know the stats on engaged employees and how that contributes to the success of a business. I strongly believe that the People function serves to balance what the company needs and what the team needs. If you can't get that balance right, you will have challenges and tension. My top priority is figuring out how to help the company and the team meet in the middle. The days of HR as a compliance function should be long gone. There is nothing more important than your people.

The top of the People function feels like a somewhat impossible role. At different times you may need to be an independent assessor, a policy architect, a firefighter, a performance coach. How do you frame your role as a People lead? And to founders reading, how should they think about the types of skills that they need in their People leader?

I think the most important thing that I can do is listen with the intention to understand perspectives and avoid misalignment. The ability to listen is very important for a People person. 

You also need to be an effective communicator - the more you communicate, and at times over communicate, the easier things can be. You must be able to translate what you hear into actionable strategies to meet business needs, and to be able to explain clearly what you’re doing, and why, in order to bring people with you on the journey. 

I care very deeply about organizational justice and the concept of fairness. Your values as a company and as leaders of the business are important, and is what will get you through the most challenging times. You need to keep falling back on these values. In a People role, you need to be the biggest champion for these, living and breathing them in everything you do.  

You're never going to be able to please everyone when designing people initiatives - it's impossible, we're all nuanced, have varying needs and interpret things differently, however if you design with organizational justice in mind, and can explain your rationale clearly and consistently whilst being able to explain to people how decisions are made, then you should be able to create an environment where people can be disappointed in particular outcomes (eg salary reviews) but can still accept that the system itself is fair.


If I had to define the purpose of the People function it would be to make the individuals in your company the competitive advantage of a business. How do you do that through your role? What experiments have you tried? What’s worked and what hasn’t?

First by listening to your team and co-creating. Do I alone really know what’s needed for a specific team or function? Definitely not, so I design processes and frameworks together with them. It pays off to design your People strategy very collaboratively with the rest of the team by gathering as much data and insight as you can across many different elements of employee engagement. At EF, we set up working groups and drew up a long list of what initiatives we could potentially do and discussed the value and the trade offs for each. It was effective because the team was part of the process and gained a deeper understanding of why we chose the things we did and also the things that we didn’t. If you communicate as openly as possible about your thinking and decision making, when things actually launch your people are already on the path of understanding.

But I would say that whatever you do, it's never done. You always have to seek feedback. You always have to iterate and innovate to make sure that things are still working for where the business is currently. My team seeks feedback on everything that we do. We do that through focus groups, pulse surveys and asking other leads in the business to hold sessions with their teams. We really measure how people feel about things, and this allows us to focus our efforts on initiatives that will have the most impact. 


You’ve had a very People-focused career but many of the People leaders I know have transitioned into that role from other functions, like sales or marketing.  Do you think that coming from those functions helps or hurts the potential effectiveness as a People lead?

I think, first and foremost, you need to have an exceptionally deep understanding of your business to be an effective people leader. That means understanding how people in every team experience life at the company: what their pressure points are, what their metrics are, etc and from there having a clear vision for how to set people up to be happy and productive in their roles. So you can definitely be effective coming from other backgrounds, especially if you’re coming to the table with well developed leadership skills. 

You get more effective with lived experience, being a “People person” may come more intuitively to some than others, but ultimately you’ll be at your best when you’ve got some lessons behind you - you’ve had the opportunity to try things and have a deeper understanding of what has worked, but also where you have failed. And of course, it is never a one size fits all, every company is different, so you need to be agile, you need to want to experiment, to seek feedback and to apply your learnings. 

I think a People background will sometimes give you an advantage where you have deeper experience in a specific area, like pay and reward - it’s hard, always hard to get reward “right”, so having a background that has exposed you to things that have worked, and things that most definitely haven’t, might give you a bit of a head start. 

For me though one of the most common mistakes which can compromise effectiveness is when the remit of your People person is not clear, or where the role is trying to be too many things. I see this quite a lot when someone with a talent background is brought on to help manage significant growth and is then also accountable as the People generalist for the business, or vice versa where a People Ops person is expected to manage the people and high volume hiring. For me these are two quite distinct skill sets, and if you’re spread too thin you’re unlikely to be highly effective in both. So being very clear about what you need this particular role to achieve, the skills and experience you need that individual to bring, and an understanding of their capacity, is really crucial to enable effectiveness. 

I also think it’s really important to assess your company’s tolerance to learn alongside someone who maybe hasn’t held a “pure” People or leadership role before - if you’re giving this opportunity to someone who is doing this for the first time, your entire organization is on that learning journey with them - for both the successes and the failures. That might work for your company, but it also might not, so again it comes back to thinking hard about what you need this role to achieve, and hiring on that basis.   


If you talk to experienced founders there's a common narrative which is, “if I can go back the one hire I’d make sooner is People / Talent”. It seems like this is a very consistently overlooked function so I’m curious of why you think that is and whether you have a suggestion of assessing when the time is right.

This is something that I have a very strong view on, which is that it’s never too early to hire a People person. The amount of People debt that you can accumulate in a relatively short space of time should not be underestimated. The decisions that you make very early in your company can still impact you two or three years down the line. At the time these may seem like very innocent decisions, but when it comes to People decisions, there's no such thing. There will always be implications for the future. Regardless of your growth journey it's super important to lay down the good foundations in People processes and practices. So even before you start growing your team, it’s never too early to hire somebody or work with a consultancy to help guide you in your people decisions. 


I’m glad you brought up consultancy. Let’s say in a different universe you’re a People consultant.  If you were hypothetically hired and you were given only one day to assess the current state of People and culture within an organization, how would you do it?

I would look at three things - although might be quite an ask for one day!

  1. Reward structure, philosophy and benchmarking

  2. Org design around leveling and progression 

  3. Maturity level of the management layer


On the first two, this is where I have seen the most people debt accumulate and it can be very difficult to unpick. The maturity of the management layer is also incredibly important. I would invest very early on in management training to support and upskill managers in the business. When you’re joining a company in a People role you're often coming into fires. Not necessarily huge fires, but People issues that can take up a lot of mental space so it can take you away from working on the high impact focus areas. Managers are the bedrock of the experience in a company. If you can develop and upskill your managers so that they’re comfortable across a wide range of People issues it makes the People lead job so much easier.

Do you find that there is a collection of skill gaps at the managerial layer?

There’s two that I commonly see. The first is around developing teams. If you don't know how to develop yourself, it can be really hard to develop other people. I see this a lot with new managers early in their careers. It’s key that you really understand how to properly focus on developing yourself, because once you're able to do that you can be much more effective with your team. This is particularly important for those that find themselves in organizations with limited opportunities for upward progression. Those managers need to put a lot of focus and effort on helping their team understand how they are still developing and growing in their current role. 

The other one, and this really comes with practice, is the ability to give constructive feedback. The feedback that really helps people to grow and learn and develop is usually not the nicest to hear. Critiquing doesn’t come easily to many so you have to put in the time and the effort to get good at delivering constructive, growth feedback in a humane but effective way. My mantra is “kind, not nice” - feedback from me always comes from a place of empathy and a desire to see people succeed. I always tell people to practice feedback conversations before going into them, so that they can get really clear on the intent behind their message. It seems really awkward but I promise you if you practice the conversation you will be much, much better at delivering the message that you want someone to hear.


On the topic of culture. It’s relatively easy to tell when things are going really great and a culture is healthy. It’s also really easy to tell when culture is broken. The in between is not so easy though. Do you have any tactics or strategies that you could advise founders on how to test their organization?

I believe full heartedly that every single person in your company should have a voice, and feel safe enough to use it. It’s important to regularly hear from the team. If you’re small enough you could do this with regular check-ins. But the larger you get, the less possible that becomes. At EF we survey the team on everything, to the point where they’re probably sick of me, but it provides us with such useful insights into the sentiment of the business. We've done engagement surveys, since I've joined EF, but in the pandemic we started to survey our people on a weekly basis. At the start we were very focused on wellbeing and were really concerned about how the pandemic would impact people's mental health. 

One of the benefits of starting that weekly pulse survey was that we embedded the routine into the team. Now we survey on a bi-monthly basis and we get good, representative participation. We look at different elements of engagement over the course of the full year, and we always include the NPS of EF as well as wellbeing to see how people are doing. That gives us the insight that we need to spot trends or dips. Our leaders receive anonymized results for their teams, all confidential of course, and are able to have follow up conversations on their own, too. As a company we can address issues proactively or adjust communications if there are general dips in sentiment. Having a system to measure team health is super helpful in remaining adaptive to the needs of our people.

One area that we disagreed on while I was at EF was the topic of performance and compensation. More specifically, I held the view that pay (salary or bonus) should be closely linked with performance reviews. Why am I incorrect in my thinking?

I don’t disagree with you - if you have people who are really good performers you should be rewarding and incentivizing them through their pay. What I am keen to avoid is overshadowing performance development conversations with an outcome that is directly tied to pay. I have often found that if you have a system that says, if you receive a four rating in your performance review you'll receive a 5% salary increase, any review conversation will completely focus on the score itself and really detract from being able to have a meaningful development conversation. This can also be really disincentivizing for people. Performance reviews should be developmental and should be there to facilitate someone's growth and success. It’s not that performance and pay should not be linked, I just believe it should be decoupled from development conversations. 

There's a debate I've had with founders with respect to managing and I’d like your take. There's one school of thought that states, to be a great leader you need to be super flexible and adjust to the styles of your people to get the most out of them. There's another school of thought that states, you as a leader need to really know yourself and assemble people around you that works with your style. Where do you fall on that spectrum?

I think that as a leader it’s very important to really understand yourself, your strengths, and your weaknesses. I also think that it is important to adapt to the needs of your team. I am of the view that a leader should seek out complimentary but different skills and perspectives. I like having people who are able to challenge me and present points of view that I might not otherwise have had. For me there's strength in having a team that’s very different from each other. You get to better conclusions and better outcomes by having people think differently from one another. If you have built trust based relationships that can weather storms, tension can be a huge positive.


I am reminded of my Facet5 that I did with you and I'm curious why you've chosen that particular test as your preferred personality assessment? What do you say to people that are dismissive of such tests?

I've worked with various different psychometric tests in the past and I like Facet5 because it provides a simple, common language for global companies. It can be used very effectively across different locations and different teams. To be a facilitator or practitioner in any of the psychometric tests you’ll have to go through some training to get the accreditation and the depth of Facet5 training is really intensive.  That education and knowledge of applying the tool is what makes it useful. The power from any psychometric test is not the results itself, but the debrief that your practitioner will take you through and the conversations that this enables. 

The real benefit comes from having a deeper understanding of yourself, and critically, how you might appear to others. Testing can help to break down any misunderstandings or tension by understanding how two people can approach the same situation in very different ways. I find it really effective for resolving relationship issues that are showing signs of strain, and it also allows for a great team building framework, too.

And as for the critics - I’ve met a fair few in my time, and I’ve never had someone walk away from a debrief who hasn’t found at least some value in it, so my advice to the cynics would be, try it - you never know what you might learn about yourself or others!  


I’d like to do a quick fire round where I ask what do people get wrong with X and then ask you a bunch of things and see what your immediate reaction is. So broadly speaking, what do you most companies get wrong with:

  • Titles: Over inflating them

  • Salary bands: inconsistent application leading to pay inequity

  • Performance Measurement: Not being clear or aligned on the expected outcomes.

  • Performance bonuses: This is a topic which I could spend many hours on. I've seen bonuses disincentivize people because they're not tightly aligned to outcomes. When you design performance bonuses you have to make sure that individuals know which levers they can pull to meet their desired outcomes.

  • Equity packages: Communication of the potential upside - too far away, too abstract

  • Onboarding: not setting clear success metrics / expectations for your ramp up in role

  • Internal promotion vs, external hiring: Internal promotion every time. Or every time where possible. Unless you're hiring a very specific skill set or experience, or the internal gap is just too large vs your immediate need, I’d always prefer internally developing your team.

What would you tell founders who know instinctively that their culture isn't working right but they're worried about bringing on a People person because they're worried about going corporate?

Your people team should be at the heart of your business, as a value-add function. Figure out what it is you want your People team to do. If you want to have a really forward thinking, innovative People function then look for someone that is as excited about that reality as you are. 

You need to know what you want before you waste your time searching. Have a vision in your mind about what this is and then design your interview process to assess that. And remember to always come back to your values - it's imperative that you find a People person who aligns with those. That’s your guiding star. And when they are in, invest in that relationship and focus on establishing trust between the two of you really early on - it’s crucial!


Lastly, what would you say to a younger talent that's really interested in the human side of business and companies, but is worried about becoming labeled like an HR bureaucrat?

There’s never been a more exciting time to be in People. The way that we work is changing, obviously accelerated by the pandemic. it's an exceptionally exciting time. if you're curious about people, if you love understanding what makes people tick, if you have a lot of resilience (because you’ll need a lot of it), if you love to listen and are fascinated by different perspectives and expectations that individuals bring into a team then there's no doubt that you can find a really fulfilling career in the People space.


First On is an attempt to uncover functional greatness by asking the experts themselves. I hope you enjoy the mini-series and with enough interest I may extend this into a more ongoing effort. If you have any functions / roles you’d like covered or have ideas for future guests please let me know.

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