How to Develop Millennials: Delegate More (with Guidelines)


On a flight home from a recent client engagement, I overheard a conversation between two Millennials sitting in the row behind mine. They were bemoaning how long it takes to advance at their company.

Their focus was on their boss– someone it seems who doesn’t understand how easily frustrated and impatient Millennials can become when not challenged or stimulated. Noticeably absent from the conversation was any indication that the boss in question was on the lookout for developmental opportunities that would keep these two Millennials – and lots of others – in the game.

In his book, Good Boss, Bad Boss, Stanford Professor Robert Sutton says that people do not quit bad organizations, they quit bad bosses.  One common difference between a good or bad boss is whether the manager is looking for ways to help advance the employee’s career.  An unenlightened manager may feel threatened by this idea, asking – among other things – why they’d want to develop an employee and then have them leave. However, the words of Richard Branson offer a ready response: “Train people well enough so that they can leave, treat them well enough so they don’t want to.” 

If you manage people – especially professionals in the Millennial generation – look to have regular conversations with them to learn how to spot developmental opportunities that would help them become more skilled and capable. With your direct reports’ developmental goals and interests in mind, you can scan the horizon to identify opportunities for delegating that will help them contribute in a more robust way. 

Delegating in this context is about assigning a task that will help your employee develop, gain visibility, help her attain mastery.  It’s not dumping a task that you don’t want to do.  It’s also not delegating and hovering, or delegating and saying, “Good luck with that.” 

There are a number of factors to consider when delegating. I've listed several below and key questions to ask yourself in exploring them.  

Employee Capability: What knowledge and skills has the employee demonstrated that make her a candidate for this assignment?

Employee Motivation: To what extent is the employee interested in this assignment or issue? What signs of ownership or commitment has she shown so far?

Importance: How significant is this task in relation to your group's objectives? To what extent will the work delegated impact other initiatives?

Trade-off: What task might have to be dropped off the employee's "to do" list to take on this assignment?

Time Available: What is the due date for this work? How much time do you have to do the work? Does the employee have the time to do the work?

Support Required: What level of support (time or other resources) would the employee require to complete the assignment?

Risk Level: What might be the consequences to your mission or organization's plan if the employee failed to achieve the desired results?

Impact on Morale: What impact would your decision to delegate to this employee have on the spirit or confidence of the employees or others on your team?

Development Opportunity: Will the assignment enhance the employee's capability in her current job? Is the work in line with the employee's career interests?

Bench Strength: Will the skills the employee develops on this task shore up a gap in your work group's or the organization's skill set?

A thorough delegation conversation will help you know how much support the employee will need to be successful.  This requires some thought and preparation on your part. Key questions to consider when preparing to delegate to a direct report:


  • What is the work to be done? By when?
  • What are the specific deliverables or component parts?
  • What would success look like?
  • How does this work address a work group or organization need?
  • What’s the level of importance of this task/project?


  • What are the skills or experience needed for the assignment?
  • What skills or experience does the employee bring?
  • What is the employee’s investment in the success of the project?
  • To what extent is this assignment a stretch?
  • How is the work in line with the employee’s career path?


  • What standards will guide evaluation of the product?
  • What outcomes would be unacceptable?
  • What is outside the scope of this assignment?
  • What stakeholders should be considered or consulted?
  • What other process guidelines for doing the work do you have?


  • What is the budget for the assignment?
  • What support (e.g., people, training, tools) is available?
  • Which of these resources can the employee access?
  • Which of these resources will you need to secure?
  • What training or tools will the employee require?


  • How will the employee communicate progress?
  • How often will you meet?
  • What documentation will you require?
  • Who else should be updated? How? How often?
  • How will you monitor performance and give feedback?

Final thought: It's always hard to lose an outstanding employee, but it's perhaps better to lose him to a new challenge than in a fit of frustration and disenchantment. Either way, you hate to see him go, but you probably retained him longer by providing additional challenges and in delegating to stretch and grow him. Plus, you never know when your paths will cross again and how.

About Beth O'Neill

During Beth's 22-year tenure with IA, she has served clients in the high-tech, healthcare, financial services, pharmaceuticals, biotech, and manufacturing industries, among others. She serves on IA's Board of Directors. A Connecticut native, Beth holds a bachelor's degree from Syracuse University's S.I. Newhouse School of Public Communications and The Whitman School of Management. She also holds a master's degree from the University of Hartford's School of Communication. Beth is a Professional Certified Coach (PCC) by the International Coach Federation. Beth contributed to this article in CLO Magazine, January 2011, and wrote this article on virtual teams in Training Magazine. Read a Wall Street Journal feature article about Beth's team leadership.