Far too often, when we talk about career development, it’s often treated as a solo player activity. But as just about anyone with a stacked resume will tell you, career growth is inherently multi-player.
Yes, it’s critically important to take ownership of your own career — opening yourself up to feedback, spotting opportunities to stretch your skillset, and crisping up your five-year plan. But there are other factors at play that can make the path ahead smoother or bumpier, such as managers who nurture instead of stifle your goals and choosing a company with massive growth potential.
As the former Senior Director of Talent Acquisition for Splunk, Shreya Iyer spent 11 years at the company, growing from a lead recruiter to an executive role. It’s a career journey that’s given her an appreciation for the holistic nature of talent development — it’s the right combination of folks taking ownership of their career goals, managers that support those ambitions, and a company culture that supports folks as they climb.
“If there’s one mistake I see folks make when they’re looking at their career, it’s getting too myopic about the day-to-day responsibilities, rather than looking at the bigger picture. Find the right company and the right manager, and you can take control of your desk to carve out the right role for yourself. Find yourself at the wrong company or working for the wrong manager, and you’ll hit a wall, even if you’re incredibly talented,” says Iyer.
When you reflect back on your job, you don't think about the emails you write or the slide decks you present. You think about how that work was received, and the experience of working with the people around you and within a company culture.
In this exclusive interview, Iyer imparts advice for three different personas: the individual, the manager, and the company-builder. She starts by sharing guidance for candidates looking to make their next move, unpacking why she chose Splunk in the first place and how she made the case to advance her career over the years. “People have asked me many times why I stayed at the same company for over 11 years. When you work at a fast-growing company, it’s never the same company year after year. I didn’t have to find the exciting challenges to tackle in my role each day — the challenges found me,” says Iyer.
As a manager herself, she’s also got plenty of ideas for other leaders on how to foster the career growth of their direct reports — including how to spot top-notch candidates during the interview process, and how to help strap on their rocket boosters as they climb aboard your company.
And as a startup talent executive, Iyer shares advice tailor-made for founders and people leaders on crafting the right company culture where folks can grow their careers for years to come — from lightweight ideas for early-stage startups, to more systematized tactics for companies that have started to scale. Let’s dive in.
TIPS FOR CANDIDATES: HOW TO EVALUATE IF A COMPANY WILL FOSTER CAREER GROWTH.
“First and foremost, you have to know who you are — what motivates you, and what demotivates you,” says Iyer. Her first piece of advice for sketching out your path? Close your laptop (but maybe wait until after you finish reading this article).
Make space to bring your career motivations into clearer focus.
“It’s a simple suggestion, but it really works — take time to think about it. Sometimes people approach career growth from a place of fear and anxiety. To get in the right mind space, you’ve got to take a step back,” she says. “Every time I go on vacation, I have an epiphany. Why? Because I’m not working. I’m not getting distracted by emails and Slack pings and meeting notifications.”
You have to make space to consider the deeper questions of who you are, what you’re looking for, and what’s important to you.
And when you begin peeling back the layers of your motivation at work, remember there’s much more to it than a new title or a salary bump. Iyer pulls an example from her own career: “When I was interviewing for a role at Splunk, I already had an offer in hand from another fantastic company. When I took the call with Splunk’s Head of People, Sheren Bouchakian, she was babysitting her nieces and nephews at the time, so you could hear kids running around in the background, which I really loved. The conversation felt natural and welcoming,” she says.
But there was one particular line during the interview that struck Iyer. “Sheren said, ‘Splunk is not the company that I work at — it’s my company, and I hold it as my own.’ As the child of small business owners, that really resonated with me. That business had a seat at our kitchen table, it was a member of our family. The fact that you could feel that kind of ownership at Splunk is the moment I knew the company aligned with my personal motivation,” says Iyer.
If you find yourself looking towards the five or ten-year horizon, but your vision is foggy, Iyer suggests chunking this out into three pieces: What you’re good at, what you enjoy, and how that correlates to career output. “For example, if you’re a strong writer, you could pursue a career as an attorney, you could also be in PR. Are you more intrinsically motivated by the output of PR or law?” she says.
With that framing in mind, she also suggests making the most of an under-utilized tool in your toolbelt — the informational interview. “If you see someone in a role that you’d like to learn more about that aligns with what you naturally excel at and desired output, try to get some time on their calendar. Folks tend to think no one will agree to talk to a stranger about their career. But we all have egos. If you send me a message saying, ‘Your career is incredibly interesting, and I want to learn more about how I can carve out a similar path,’ I will give you 30 minutes of my time,” says Iyer. These same informational interviews can also be used to cross paths off of the list. “Even if you want to confirm something isn’t the right career path to go down, that’s fine too — talk to those folks as well.”
When assessing a company, look for these mile markers.
When it comes to evaluating whether a startup has a promising trajectory (which in turn, means lots of green space for your own career), it’s time to put on your research hat. “Pay attention to the investment cycle. Who has invested, how much, who’s leading the round, who’s coming back to lead another round?” says Iyer.
Also, keep an eye out for movement in the C-Suite. “There are a few indicators you should look out for. When I was interviewing with Splunk, Godfrey Sullivan had just come in as CEO, and he had taken companies public before. When that changing of the guard happens, that may be a signal something big is coming,” she says.
Finally, drill down into how the particular role you’re eyeing fits into the company’s growth trajectory. “Are they investing more in channel sales or are they investing in direct? Are they investing in cloud and security? Is there global expansion happening? Are there more roles available in EMEA or APAC than you’d expect?” she says. “Their job board is a good place to snoop for signals and source more specific questions to ask in your interviews, such as ‘Talk to me about your globalization strategy? Do you have plans to expand into APAC or EMEA and, if so, what countries do you plan to start with?’”
A company’s career page will essentially tell you their product roadmap and where the company’s investing moving forward.
For a company that’s at least a couple of years old, look for folks who are sticking around and flexing different skills. “You want to see people who have been there for at least two years plus, and if they’ve been growing in their careers. This doesn’t have to just mean getting promoted with new titles — are they taking on different, interesting projects? You want to find a critical mass of folks who are growing in the company, either upwards or laterally” says Iyer.
Put career growth front and center in the interview.
While diving into company research can answer some of your questions as a potential hire, there’s no replacement for going deep in the interview. Iyer’s advice for candidates? Don’t shy away from the harder questions — set the tone for taking control of your desk during the interview process. “Ask about the one, three, five-year future where they see the company growing. Probe their goals and what they’re striving for — and more importantly, is there a clear plan around those goals? Are they just talking about strategy, principles, and values, or are they diving into execution as well?” says Iyer. Here are two specific questions that dig in here:
Where do you see your revenue growth coming from next year? “This question can be answered with industries, partnerships, ARR, etc. I like leaving some questions more open-ended — wherever the hiring manager pulls their answer from will tell you what’s top of mind for them.”
Do you see the company going public? What would need to be achieved in order to get there, and what’s your plan for achieving those goals?
And when it comes to sizing up how your own role fits in, start looking a few steps ahead. “It’s your job — own it. Ask what the career path is for the particular role you’re interviewing for. If you’re interviewing for a senior manager position, ask about what they’d look for in a director,” she says. No clear answer here is a flag that the career pathing is still in the development phase, rather than crisp and clear.
“I had someone on my team who was vocal even in the interview that she wanted to be a director one day. It’s important to speak up and say, ‘This is where I’m at today. I’m happy to be at this level flexing these skills for the next couple of years. But eventually, I want to grow towards being a director,” says Iyer.
It’s not just about being upfront that you want to be promoted — which may feel too forward for some folks. It’s about demonstrating conviction in your career path. “It goes back to embracing your responsibility for your own career.”
A lot of folks talk themselves out of being direct about their ambition because they worry it might come off as abrasive.
Iyer leverages a specific technique to soften the approach. “It’s okay to say, ‘My fear is that I’m going to come off as too arrogant, and I want to make sure that’s not the case.’ And then you say whatever point you want to make. You build the framework for how they will interpret the response and demonstrate self-awareness by acknowledging any awkwardness in advance,” she says.
Questions for candidates to ask in an interview:
As you do your interview prep, consider the questions you’ll ask of the panel that clarify whether it’s the right choice for your next move. Along with a few of Iyer’s favorites below, check out this Review article with 40 other questions to consider adding to your list.
What initiatives were rolled out that changed the course of the product or the GTM strategy? “I love this question because we can talk about principles and values until we’re blue in the face. It’s important to show how you actually executed on it. This question yields a definitive answer.”
What’s the most common reason people leave here and what’s the company doing to rectify it?
What are the most common reasons to promote people here? Why did you promote your last report? “In thinking about how I might answer this question as a hiring manager, my direct report I mentioned is a perfect example. I promoted her because she was really intentional about her job and her career growth. Of course, she was a hard worker. But what really set her apart from others is how she had taken extreme ownership of her job. Managers should have answers to these questions about how folks move upwards — otherwise, it means they haven’t made internal mobility a priority. Anyone can say we believe in upward mobility, but saying, "I have five reports, two have been promoted and two have taken on more global responsibility," shows their values and actions align.”
If you were to bucket my role, how would you break down what I’d spend an average day doing?
What percentage of your role tends to be more tactical versus more strategic? “Typically, companies don’t want to do a bait and switch. At a startup, even high-level leaders will likely be expected to roll up their sleeves. When I came on board at Splunk, I joined a very small team. You were expected to take on the tactical, administrative tasks at the beginning, and then move into strategy as the company grew.”
What metrics do I need to achieve to be able to be successful in my role? What challenges are in my way and what are your thoughts on how to overcome those challenges?
HOW TO GROW YOUR CAREER BY ALIGNING THE COMPANY NEEDS WITH YOUR OWN ASPIRATIONS.
After climbing aboard a startup, far too often Iyer sees folks shrink their frame of reference, missing the forest for the trees. “You shouldn’t limit yourself to roles that have already been created. Pay attention to your own skill-sets, passions and goals that may overlap with untapped opportunities. What role can I create for myself that others will support because there’s value to be added?” says Iyer. (One tip here? Look for folks at the company who are trying to give away their Legos.)
When it comes to spotting those onramps, keep in mind that the greatest opportunities for growth are at the intersection of the needs of the business, and flexing your metaphorical muscles. “Why would the higher-ups say yes to your proposal? That’s how you need to frame your growth opportunities. There has to be data behind your position,” says Iyer.
She sketches out an example from her own career at Splunk. “When I first came in, as is commonly the case for early-stage companies, we were using agencies constantly for our recruiting. And there were some leaders that wanted to continue to use those agencies rather than build up our internal recruiting because it’s what they were used to. Not only would it be beneficial for the company to build out its internal recruiting team, but it was also an exciting challenge for my own career to spearhead that project,” says Iyer.
In making her pitch to senior leadership, Iyer led with the bottom line. “There would be huge cost savings, so I led with the framing that it would save X amount per every hire to create an internal recruiting team. I stayed focused on the company upside, rather than what it would do to advance my own personal career goals,” she says.
When you present a new project or make your case for taking on a new role, always start from the framing of: Why would they say yes to this suggestion? Dangle the carrot.
TIPS FOR HIRING MANAGERS: HOW TO FIND FOLKS LOOKING TO GROW IN THEIR CAREER (AND THEN HOW TO SUPPORT THEM ALONG THAT PATH)
Next, Iyer turns her attention to hiring managers who are on the hunt for candidates with big ambitions. When it comes to sizing up career growth potential, one of the most frequent missteps Iyer sees from managers is discounting candidates who have job hopped, with a resume marked by shorter stints in different roles. “I think it’s a mistake when people assume job-hopping is a red flag. It’s a yellow flag — you need to dig in deeper. Are they job-hopping because their role and their career is growing, or are they job-hopping because of a lack of focus?” she says.
Iyer suggests a couple of options for opening up the conversation with candidates:
“I noticed you were at your last three companies for under two years. Can you tell me a bit about why you weren’t there for a longer period of time?”
“We want someone who is willing to plant roots with us. The last two companies you were at you left in less than two years. Can you explain the why behind your decision and why you believe you’d stay with us longer?”
When it comes to sussing out green-flag answers from candidates, look for folks who have self-awareness around the story their resume is telling. “You want them to have expected the question. They know how it might look and are ready to address it. They’re able to articulate why they moved into each role because of the opportunity it lent them. They’re intentional about the goals for each step of their career, and how each job on their resume has put them closer to those goals,” says Iyer.
On the flip side, be wary of folks who are defensive when questioned about their resume. “If they’re making excuses rather than giving you the reasoning behind each job switch, that’s a red flag. They won’t be open to feedback, or they’re quick to defend. A common response you might hear is, ‘Well, everyone does it, that’s just how it works in our industry,’” she says. “Also be wary of lots of interpersonal issues cropping up. We’ve all been there when you don’t click with a manager or a team. But if it’s happening in your career multiple times, and they aren’t clearly able to explain where their values were misaligned, then there’s probably a lack of self-awareness at play.”
Questions for managers to ask in an interview:
Iyer lists a few of her favorite questions she leans on as a hiring manager — check out more from the First Round community here.
Tell me about a time when you achieved success entirely on your own? “This is a trick question and one that tests humility and self-awareness. Because, at the end of the day, there's really nothing we've done successfully that isn't attributable to a team, partner, client, manager or just someone paving the way before us.”
What are you working to get better at? Tell me about a time you’ve failed. “These are both frequently used, but I like using these sorts of open-ended questions and seeing how the candidate interprets them. Some answer with a skillset, others answer it more personally. Some give canned answers, others are very honest. This can give you an insight into their personality and how they handle discomfort.”
What motivates you? “People can answer this in a lot of different ways, but they will always answer with what’s most important to them. If they’re motivated by stepping into the next phase of their career, it will show up here.”
We love professionals who want to grow into their niche and we also value those who want to climb the ranks. Which are you? “There’s no right answer here. Some folks want to become a really incredible IC with deep expertise. Others want to grow in a leadership position. You’re looking for clarity of conviction in their career path and what’s most important to them.”
Retain your top talent:
Of course, hiring motivated folks is just the first step — managers also need to lay the groundwork for a smoother path ahead.
Set the tone: “Many reports think it’s solely the manager’s job to uplevel their careers. But career growth is the report’s responsibility, not the manager’s. As a manager, emphasize early on that you expect your hire to take control of their own desk, and you will support those goals and provide feedback along the way.”
Keep them challenged: “This starts with finding out their motivators. Are they most motivated by impact, title, collaboration, etc? This will point you towards how to uplevel them. Explain that upward mobility doesn’t always mean a promotion — it means growing skillsets and capabilities. Managers can’t promote everyone, and even the best ICs may not make the best managers. Reframe what upward success looks like, whether that be leading a new project, a global initiative, or going through some training.”
Assign a rotating Devil’s Advocate: “Whether it’s for a team, a project or a meeting, try assigning one person on the team to challenge the team to think with different frameworks. In the process, it will also push them to develop their critical thinking skills. Oftentimes we readily accept limitations, even while openly expressing our desire to be disruptive. Disruption starts with questioning the premise. The Devil’s Advocate exercise helps people start to do that and, in turn, think more critically.”
Create the culture for your team: “Just because the company you work for has its own culture, doesn’t mean you’re not also responsible for creating a culture within your smaller team. As a leader, it’s your job to set that tone. What sort of rituals feel authentic to you as a leader and the team that you’ve built?”
TIPS FOR COMPANIES: HOW TO CRAFT A COMPANY CULTURE THAT ATTRACTS AND RETAINS TOP TALENT.
The fight for top-notch talent affects just about every company and industry — from BigCos to tiny startups. But without headline-grabbing brand recognition, startups often have extra hurdles to clear.
Skip the buzzwords and lead with authenticity.
When it comes to honing your employer brand to attract top-notch candidates, Iyer warns folks to stay away from overwrought startup cliches. “When you’re starting a company, you want to attract creative types and innovators. This means you have to stay away from the same overused phrases everyone else is using. ‘We have so-and-so VC backing us. That’s important information for candidates, but it can’t be your only selling point. There are probably 300 other companies backed by that same VC. What makes you special?” says Iyer.
You see this employer branding all the time — “We’re the next big startup. We’re the next unicorn.” Those terms have been beaten to death. What makes your company original?
And in her experience, the answer to the, ‘What’s your differentiator?’ question doesn’t even need to be so serious. “Before anyone knew what Splunk was, they’d probably seen the company on our swag. We had a penchant for funny t-shirts, with phrases like ‘Take the SH out of IT,’ or ‘I like Big Data and I cannot lie.’ Maybe folks rolled their eyes a bit, but they remembered us,” says Iyer.
“One of our founders, Eric Swan, would make comments in interviews that Splunk was actually just a t-shirt company that happens to sell software. The company really embraced that humility as part of our character, and that low-ego culture shone through in our interviews with candidates,” she says.
Don’t just save career development for when you’re a BigCo — look for lightweight exercises to start building your muscles.
With a long list of items on a startup’s to-do list, career development often falls to the bottom — designated as a nice-to-have. After all, what’s the rush to create all sorts of levels and promotion criteria when there are just a few dozen folks at the company? But just like your product strategy or brand-building, you’ve got to lay the foundation for these future building blocks to sit upon.
For very early-stage startups, it may be too early to implement formal manager training, but there are some lightweight ideas for baking career development into your company DNA from the start. “Think about how you can institute some mentorship or shadowing programs — giving folks the opportunity to spend an hour a week with a more senior person on the team, to learn more about how they work. Or senior folks in a meeting carving out the time to share more about their thought process behind a specific decision,” says Iyer.
But there are a few key signals that indicate it might be time to add on more formal systems here. “Are you starting to lose employees to a certain set of companies? What are they doing well that you’re lacking in?” she says. While not an exact number, she suggests a general rule of thumb to look out for: “What percentage of your employees have been in the same role for 18 months? They may not be speaking up that they want more opportunities — or sometimes they speak up when they finally quit. You don’t want to wait until that resignation to realize it was time to move them up or laterally.”
Another lightweight idea for career development is just making sure you’re advertising the opportunities that are already available. “When Splunk was very young, we would just send out a weekly email to the whole company that highlighted a few interesting roles, with a call to action for any internal folks to reach out if they’re interested. As the company grows, you may create an intranet or a specific career channel on Slack. But in the beginning, it’s just about continuously banging that drum,” she says.
Invest in folks who can take your career development plan to the next level.
“There's the oft-repeated quote: ‘Don't tell me your values, show me your budget and I'll tell you your values.’ Are you serious about career development or are you doing this in name only?” says Iyer.
For founders performing their own self-assessment, there are a few benchmarks to hold yourself to: “Investing in HR is incredibly important — because these are the folks who will create the machinery for career development, like training for managers and ICs, interview training, intentional career paths for different roles, performance review cycles, etc.” she says.
How much you invest is another clue: “Are all the folks on your HR team early in their careers, or are you investing in senior talent? These are the folks who can get creative with how career development can be unique to your company culture. Training is one method, but maybe instead of an education budget, you give employees X number of dollars a year to hire a leadership coach. Junior HR employees will likely only be able to execute from established playbooks, versus looking at the problem from first principles. You need senior input,” says Iyer.
She also pushes founders to look at a more holistic picture, rather than just the foreground. “When I talk about career development, folks are often surprised because I take it several steps back into workforce planning and org design. Why does it start with org design? Because there have been times in my own career where there’s been career training or an education stipend available to me and I have not taken it, because I’ve been way too busy,” says Iyer.
“Let’s say a manager is a rising star at the company. Often the instinct here is to then give them more opportunities to grow — four open headcount positions, plus a new global project. But they aren’t going to be in a strong position to grow in their career, because they’re operating purely tactically at that point,” she says. “You have to be really thoughtful about giving folks space to think and grow — if folks don’t have the bandwidth, any career planning initiatives are dead in the water.”
Be specific here as you set your quarterly and annual goals. “Make this explicit — like reserving 5% folks’ role reserved for career growth, whether that’s taking a course, attending training, etc. Or reserve 15% of their week for project work. Taking on new stretch projects can be where the most growth happens, but if the org hasn’t created the bandwidth for it as part of your role, it can become overwhelming rather than an opportunity to learn,” says Iyer.
Leaders have to strategically think about how to achieve their deliverables while enabling their team to grow and elevate. We often treat these two factors as incongruent, but they’re foundational to each other.
Cover image by Getty Images / AntonioSolano