Retaining Ambitious Talent in a Conservative Organization

In the increasingly competitive market for top talent, aptly coined the ‘War for Talent’, retaining top HR and Recruiting professionals is just...


Lauren Pease

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In the increasingly competitive market for top talent, aptly coined the ‘War for Talent’, retaining top HR and Recruiting professionals is just as challenging as it is for the business groups we support. Ambitious professionals have their pick of employers. Let’s assume that you’ve succeeded in attracting and subsequently hiring a superstar. Your next challenge is to keep them. To maximize retention of the all-time greats, how does the best leader run his or her team? In three words: like a startup.

I began my career at a startup, then worked for three Global Fortune 500s, and most recently returned to the startup world. With an MBA in Leadership and Change Management from NYU’s Stern School of Business, I have studied and worked with a wide range of leadership styles. As this article was coming together, I connected with strong talent I’ve been lucky enough to work with throughout my career (some of whom I hired and personally led). There is widespread consensus on the key elements that enable them to perform their best, and subsequently make them want to stay. Interestingly, from observing leaders in many types of organizations, startups seem better equipped than most (but, not all!) Fortune 500s to meet the development expectations of top performers.

1. Diversity (of Experience) is King
The General Athlete is the employee that can be a power player anywhere you put them.  In a startup, even specialists with deep expertise contribute to other areas within which they can both learn and add value. Whether this approach is intentional or simply due to lack of resources, the benefit is arguably the development of fulfilled, well-rounded employees. I’ve seen a General Counsel that is a marketing leader, HR Generalists that are benefits and onboarding specialists, and Recruiting Coordinators that can build killer business cases and provide thought leadership on organizational design.

In more established organizations, there are often more boundaries around specific job functions, especially when leaders only focus on the immediate tasks at hand. While less ambitious team members may be content to accept this, your A-players might seek external opportunities to gain the development that keeps them stimulated. Leaders can take simple steps to enhance the experience of your top talent without upending the org chart. Depending on your company’s culture and flexibility, some actionable examples include:

  • Bring early career team members into manager-level discussions as observers;
  • Ask for their opinions and inject questions to help refine their thinking;
  • Learn about their long-term career objectives and identify (or create!) projects that will build skillsets in these areas; and
  • Rotate responsibilities for project management to offer on-the-job “internships” across functional areas.

2. Leaders should keep their doors open
Leaders at all levels within startups are accessible to the majority of the organization. Even when there are multiple levels of management, the most junior team members have a direct line to the CEO. The CEO knows them by name, knows what is going on in their lives, and truly cares about them. Everyone is empowered to provide feedback both directly to team members and to leadership and, in this open environment, everyone benefits. In cases where more opinions create disagreement and debate, this challenges the final decision and thereby drives smarter decision-making.

To be clear, I realize not everyone can or should have access to the CEO of a Fortune 500 organization; however, companies will greatly benefit when senior leaders with responsibility for a function (Directors, Global Directors and E/SVPs who report into the CHRO) should have a genuinely open line of communication to the most junior team members within their functions. When this is genuinely (and not just rhetorically) available, and when leaders seek out honest feedback and safeguard the sacredness of this input, their team members will feel empowered to share process improvement possibilities, manager development opportunities, and feel that their perspective is valued.

3. Environment is everything — create one that fosters innovation
The startup environment gives a freedom for innovation which, in turn, fosters the learning and development of team members. This innovative drive in startups is fostered by the presence of fewer managers and a culture focused on collaboration, rather than blame. Let’s take a look at Israel, which is often called  the “Startup Nation,” being second only to Silicon Valley in its number of startups even though it’s the size of New Jersey. Many have studied the conditions that create this hotbed of innovation, and, in a country where military service is mandatory, one statistic is particularly striking: Israeli military leaders are in charge of troops at a ratio of 1:9, which is a stunningly large amount of troops being managed by each commander (for comparison, the US military runs at a ratio of 1:5). It means that the Israeli front lines must make more decisions on the fly, which they learn to do extremely well. Studies have found this huge freedom to work and make mistakes in the army is a large factor that permeates into Israel’s innovative startup culture, and there’s a lesson here for leaders looking to retain and develop talent.

To replicate the conditions that foster innovation, there are two key actions great leaders employ:  (1) when faced with a choice, they choose workers over managers, and (2) they create a blame-free culture. First, less layers of middle management forces your team to be independent and make their own decisions. If you are resource-rich enough to get both leaders and workers, then encourage your managers to give their direct reports the independence to innovate and solve problems on their own. Ensure leaders give team members sufficient boundaries to keep them safe but enough latitude to make correctable mistakes from which they can learn. Second, ensure your managers support team members’ learning and development. Team members who know they are supported by leadership in all circumstances, in both successes and mistakes, will feel free enough to experiment and thus empowered by the opportunities handed to them. When errors occur, managers must be trusted to collaborate with their team to put controls in place to avoid future or repeat errors (which helps everyone learn further).

4. Clarity of path, not just end-point
In successful startups, the vision is clear. The team comes to work every day to collaborate and build for the future. Everyone has the map, knows the destination, and rows together to get there, no matter how rough the seas get.

In larger organizations, the vision is usually created by leadership and passed down without input flowing upstream. Work feels more analogous to putting oil and gas into a car to keep it running, rather than being a part of designing and building the car to perform at its peak level. Large organizations are at a disadvantage here, as it’s much harder to understand how the work you put in each day makes a tangible impact on the products or services you provide to your customers. That said, great leaders should focus on how every team member, senior and junior, can understand the critical part they play in carrying out the company’s vision. Offering your team members the opportunity to craft team-wide objectives, identify projects they’d like to add to the roadmap and participate in the selection process for new team members are a few examples of areas where team members can feel included in the vision and overall direction of the team.

In conclusion, taking the lead from your startup kin (after all, we were all startups once) can help us retain our top talent as long as possible. It is in this leadership fashion that, when the talent does inevitably move on (because gone are the days of lifetime loyalty to one company), we can celebrate it as a collective success in the ways we helped encourage and develop them, rather than wonder what we could have done to make them stay.

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