The fog of war envelops every battlefield. When the plan breaks down amid the chaos and ambiguity, how do young Marines know what to do next? How can they take relevant action in the present when their carefully detailed plan has been rendered useless? Every leader communicates something called Commander’s Intent — effectively an end state or envisioned future of the battlefield when all is said and done. Understanding this vision, even the most green Marines can take decisive, relevant action right now. Managers should equip their people to achieve the same level of clarity in their careers, says Candor, Inc. co-founder and COO and former military leader Russ Laraway.



Laraway believes that managers can grow and retain top talent by helping their employees articulate long-term vision for their careers. His approach has made him a sought-after advisor on the issue of employee retention and talent development. While at Google, his framework for career development led to more than a 10-point bump on engagement scores across hundreds of employees. In addition to Google, Laraway’s career spans operational and management roles at Twitter, founding and leading his own supply chain consulting firm and serving as a Company Commander in the Marine Corps, in which he oversaw 175 Marines.

Drawing from his talk at First Round’s CEO Summit and additional conversations, Laraway explains a servant leader’s approach to career conversations, a tool that accelerates development, enhances engagement and boosts retention in teams. He lays out a step-by-step approach for creating meaningful dialogue and details pitfalls to avoid. Any startup seeking to keep its talent for the long term will gain helpful tips from Laraway’s framework.

Why Career Conversations Are Your Secret Weapon

Companies face both a threat and an opportunity when it comes to their employees’ long term career aspirations. First, the threat: if managers just lead their employees merely with the day-to-day in mind, they’ll lose some of their best people sooner than they might have otherwise. Laraway has found that career conversations — deep, meaningful dialogue coupled with action plans around measurable goals — go a long way in keeping them around for longer.

Conversely, the opportunity when it comes to managing your people is the chance to be a servant leader, a concept coined in the 1970s that says the best leaders live to be in service to their teams. “One way to know if you’re exhibiting service leadership,” Laraway says, citing leadership expert Robert Greenleaf, “is if the people under you are growing and developing.”

“I've seen this play out in practice over and over and over. People are surprised that they can grow towards their dreams and stay put in their current role,” says Laraway. “This is one of the side benefits to this approach to career conversations. It can reduce any ants-in-the-pants of wanting to leave or be promoted. As a manager, one of your prime jobs is to help the people on your team develop.”

Leaders, do you have what you need to invest in your people with the same focus and fervor you want them to give your company?

Candor, Inc.'s COO Russ Laraway speaks at First Round's CEO Summit.

Four Ways To Screw Up Career Conversations

“You have to be careful not to take shortcuts around this initiative,” Laraway cautions. “Your people will grow with or without you. The question is who will they grow into?”

Laraway has refined a process for figuring that out. He outlines four approaches to career conversations that frequently backfire:

Don’t have them at all. “The first problem with career conversations is that they’re not happening. A lot of times, folks don't know it’s their duty to talk to someone about their career. Or, if they do realize it, they don't know exactly what to do,” Laraway says. “Even worse, there are ‘imposter conversations,’ such as performance reviews, which are inherently backward looking, whereas good career conversations are mostly focused on a dream in the future.”

Performance reviews are backwards-looking, while career conversations are forward-looking. Performance reviews ≠ career conversations.

Limit them to the near future. “In thinking about career conversations, the short term is not a good way to think. The idea that discussing promotion equals discussing career? Nope,” Laraway says. “Promotions, at their very best, represent an incremental increase in scope and growth. At their worst, they're nothing more than a title and comp change, a nice formal recognition for a job well done. Promotion conversations do not equal career conversations.”

Just check the box. “Big Bad Company Inc.’s CEO convenes all the VPs and they put up on the screen the recent scores from the engagement survey. They discover that in three to five years, a bunch of people are going to leave because they're concerned about career growth and development. Panic ensues,” says Laraway. “I’ve seen this a number of times in more than one company. An HR person chimes in and says, ‘You know what? We've got to get everybody on an IDP, an individual development plan.’ Boom. Problem solved. The VPs, desperate for action, say ‘Yes!’ and relay the message down the line to directors, managers and their teams. Employees burn their weekends putting together their IDPs. Monday comes. They say, ‘Got my IDP.’ Box checked, squared away. Then no one looks at the IDPs again. It is a terrible process, but the box has been checked. That's a problem.”

Improvise. People sometimes approach career planning in a start-and-stop, half-baked way. “We plan a lot of things. We plan our families, plan our weekends, plan our vacations and plan our meals,” says Laraway. “It’s a little crazy to me that we don't often put a lot of energy, intentionality, or conscientiousness toward our careers. We need to put a little more structure around that.”

The way to fix this imbalance is to follow the framework Laraway lays out for developing career action plans and having serious, meaningful — and even amazing — conversations with your employees. By doing that, you can really help them grow towards their dreams. By investing in your people in this highly differentiated way, often they’ll say, “I’m growing and my manager has my back. The grass isn’t always greener on the other side.”

It’s hard to keep books upright without bookends. You must understand someone's past and future to know how to order the present.

Three Career Conversations You Should be Having

A decade ago, in a conversation about career planning, Sheryl Sandberg told Laraway, “You have to have a long-term vision and an 18-month plan.” Her advice was in response to some flawed thinking that she'd observed in how people — including herself — were thinking about their careers. She talked about two broad problems. First, people are inclined to plan their careers step-by-step, the mistake she made. “Or they do no planning at all,” Laraway says. “If she’d have stuck with that very carefully designed plan from earlier in her career, she would have not taken that Google opportunity, which was a very meaningful slope-changer in her career trajectory.”

Instead, take another path forward when it comes to career conversations. Laraway breaks down a three-step process for helping your employees develop both short- and long-term plans. Each of these steps involves about an hour of investment approximately two weeks apart from one another. These three approaches help surface the key components of your employee’s path: their past, present and future.

1. Be their Barbara Walters. Take an hour to get to know your employees — deeply. Begin with the phrase:

Starting with kindergarten, tell me about your life.

Then probe with more questions when they talk about pivots in their lives.

Laraway took this tactic with a direct report, who mentioned switching from cheerleading to swimming while in high school. “I became curious about why she liked swimming so much better than cheerleading. ‘What was it about swimming?’ She said, ‘I never really thought about it, but when we worked hard and we spent a lot of time in that pool, we had tangible outcomes on the backend. We reduced our times or maybe even got to the podium,’” says Laraway. “It became really clear through that story, and others like it throughout her life, that she deeply valued hard work leading to tangible outcomes. It was so clear to both of us because of the story.”

Look for the patterns over the course of your people's lives that give you strong signal and just write them down. “In this case of the cheerleader-turned-swimmer, I wrote, ‘Hard work leads to tangible outcomes.’ Then I wrote down the story, ‘Cheerleader to swimmer,’” Laraway says. “It’s not rocket science. I had pages of notes that yielded a list of 5-10 values and motivators that helped us have a shared, textured understanding of what she cared about and what brought her to this point."

2. Spot their lighthouse and bring it into focus. Articulating a clear vision for an employee’s future is the most important step. Ask your employee about their dreams.

“Maybe we're a little skeptical that a lot of our millennials, for example, will know what they want to be when they grow up. In fact, some of you are thinking that you don't even know what you want to be when you grow up. That's common skepticism,” Laraway concedes, but he continues, “I've run this process hundreds of times, and never had a person who couldn't tell me about their dreams.”

“The idea is to try to get employees to start to talk to you about their dreams, or three to five of them if they don't really want to commit to one idea. None of it should be time-bound — no 10-year plans. Ask what this person would be doing at the pinnacle of his or her career — when they’re feeling challenged, engaged and not wanting anything else.”

“What we have now is a blurry, fuzzy lighthouse out in the distance. The goal is to try to bring that lighthouse into focus. We want to see the paint chips. We want to see the red tiles on top. We want to see the seagull perched on it. We've got to ask a few more questions,” Laraway says. He suggests the following three questions for focusing the vision only after you both understand the dream:

What size company do you imagine working for?

What industry do you want to be in?

Do you want to be in a very senior individual contributor type role or very senior management type role?

Russ Laraway

Laraway had an employee, Jane, who articulated this vision: Own and operate my own spirulina farm.

This woman had also noted in her life story conversation that the happiest she ever was in her career was when she “built something from nothing” at a former employer, so this vision was aligned with what she valued most. Knowing her wildest dreams helped Laraway place her in a position that would deliver experiences that would compound and prepare her for where she was headed — even if she was in a different industry currently. “We were working in digital ads at the time at Google. Together, we were able to take the right actions given her vision, and advocate for her to get training that would be valuable for her as an entrepreneur,” Laraway says. “We were both extremely happy with the investment we made in her. She stayed at Google longer than I did, and continues to grow in the digital ad space at Facebook. The spirulina farm is still the lighthouse in the distance, and that’s ok.”

3. Create a career action plan. Armed with a shared and textured understanding of your employees’ key motivators, and a clear articulation of their own envisioned future, now you’re ready for the next step: crafting a detailed action plan. These will map out — in great detail — exactly how your employee is going to reach that vision for themselves. Think of it as a roadmap to self-actualization.

“Now we've got it: We've got an understanding of the person’s origin, path taken to this point, what they care about and what drives them. Now we've got a clear idea of this lighthouse in the distance. We know their dreams — what lights them up. We know how they envision their future,” says Laraway. “That arms us with all we need to take relevant action right now and start to build the career action plan.”

Four Steps to Design a Career Action Plan

At Candor, career action plans are developed into four parts. Each part has 2-5 action items. Each action item should answer: Who will do what by when?

“If those three questions aren't answered, you don't have an action plan. What you have is that IDP exercise. Who will do what by when? That's an accountable plan. That's something you can work on and manage toward,” Laraway says.

Here’s how career action plans should be created:

Develop their role. If you understand where employees are trying to go, you can make adjustments in their current role to move them in the right direction. “A lot of times when we think about career, we’re a broken record, stuck on: what's next, what's next, what's next. People are hungry to know what their next job will be, or when that next promotion is coming,” Laraway says. “If people feel like they've got a manager who's got their back and investing them in a differentiated way, it’s a different result. If we’re being explicit about doing some things in their current role that can take them toward the end goal in their career, that helps reduce the ants in their pants a little bit. People tend to want to stay put.”

Enhance their network. Help them identify the people who can inform and influence where they’re trying to go. “This can entail everything from helping set up informational interviews to being their sounding board to help pressure-test their thinking,” says Laraway. “Influence is pretty straightforward. Who are the people that can help uncover opportunities that'll take them closer to their long-term career vision? Identify those people and help them get some meetings.”

Laraway stresses that it’s a way of providing 360-degree support to your employee. “The more they explore future possibilities, the more they’ll be engaged in their work. Meeting people who are in their dream industry or job can be inspiring and clarifying. It also helps forge connections that may come in handy down the line,” Laraway says. “And it yields benefits for you, too. It’s so important for your employee to know how much you’re supportive of them, and how far you’re willing to go to make sure they achieve their dream job. That inspires loyalty like nothing else.”

Define their immediate next step. “Let's be explicit about what the next step or role you will fill that makes sense, given what you care about, the path behind you, and the lighthouse off in the distance,” Laraway says. “It can involve advocating for them to make a lateral or vertical move, or giving them goalposts to hit on a quarterly basis. You want to help them gain crystal clarity that this immediate next step is a logical one en route to their dreams.”

Enlist others to help hone their skills. Send your employees to training like conferences or workshops. But be mindful that you’re sending them to opportunities that actually make sense in the context of the long-term vision. For example, Laraway cites a highly popular Advanced Negotiations course that every single person wanted to take at the Wharton School — even if there was no clear reason why he or she needed it.

It sounded strategic and cool, so people were interested in the course, but they couldn’t explain why they needed it to justify it expensive price tag. “On the other hand, I had a person with a career vision to lead the business development function for one of the big like video platforms, like Netflix,” says Laraway. “It's a pretty defined, compelling vision. It made a lot of sense for me to try to get that investment for that person to get them to the advanced negotiations class because clearly that's a big part of any business development role.”

When you understand someone's long-term career vision, it helps put training investments into context.

Nurturing Employees as a Winning Strategy

Managers have the opportunity for service leadership but still must cope with the threat of good people leaving the organization. The key here is to intently invest in each employee, making sure they’re getting — and know that they’re getting — the tools and experiences they need to advance in the way they aspire to advance. No empty promotions or ceremonial performance reviews. Instead, aim for real, honest conversations that unearth your employees’ hopes and dreams, and shed light on their past and future. Doing so can extend the life of employees at your company, but also bring clarity to how and when they should embark on the next stage in pursuit of their dreams.

“A manager’s job is to guide a team to deliver results, and she’s able to do that well in a sustained way — not because she exhibits power, control, or authority, but because she nurtures and enhances a set of human relationships around her. What’s more, she’s developed those relationships by crafting a long-term vision,” Laraway says. “It’s that same zooming out that guides a Marine in the fog of war. The Marine knows what the end state is supposed to look like and he can move people toward that end. Armed with the clear vision of the end state, he's able to take relevant action today. That’s the clarity in the chaos. That turns a job into a through line for a person’s career. The more you can help them along their path, the more they’ll likely to stay and help your company on its journey.”