David Kincaid, CEO and Owner of Level Five Strategic Advisors, chats over a beer with employee Ben Wise, a Brand Analyst, in the bar below their office on July 15, 2010. Kincaid holds a draw for his employees and the winner gets to have drinks with him, their boss.JENNIFER ROBERTS FOR THE GLOBE AND MAIL
Having been on the job for less than a year, there were many things that brand analyst Ben Wise wanted to know about his company's goals and how he fit into them.
So, as bold as it might seem, he invited his chief executive officer out to a local brew pub for a beer and a talk about his future.
David Kincaid, CEO of Toronto consultancy Level5 Strategic Brand Advisors, accepted the invitation. He was also immediately open to Mr. Wise's suggestion that the company set up a blog, and put Mr. Wise in charge of developing one.
"It was a very productive discussion. It was definitely helpful to get clear on what the company needs and how I can get the best opportunities to learn, take on more responsibility and advance," said Mr. Wise, 27.
His experience should inspire others to take the initiative to grab face time with the boss, especially at this time of year, when things tend to be slower, career experts say. With so many people on vacation there are likely to be fewer demands on busy executives. The season also brings events such as company barbecues or golf tournaments that create opportunities to have an informal chat with the boss.
But how do you make your personal encounter worth his or her worthwhile? And what should you discuss to develop a higher profile with the boss - or your bosses' boss - in the future? We asked the experts.
GET ON THE RADAR
The fact that you are around the office when others aren't works in your favour, so manage your optics to be as visible as possible, recommends Allison Graham, principal of London, Ont.-based Elevate Seminars and Strategic Development Inc. and author of Business Cards to Business Relationships. "If your employer likes to go to the office early, be an early bird and have an idea you can present quickly in an encounter in the elevator or coffee room. Or you might just walk by the office and give a quick and cheerful "good morning" to signal that you're on the job bright and early too," she said .
LET'S DO LUNCH?
Daunting though it may seem, your boss might accept an invitation to lunch to get to know you better, said Tim Cork, president of career transition company NexCareer Inc. in Toronto and author of an advice book, Tapping the Iceberg. But groundwork must be laid. You might put someone you barely know on the spot if you ask him or her to commit to a full hour. It is best to keep your approach simple and subtle. "Say [that]you are hoping there might be an opportune time to sit down and get some ideas based on their experience of how you can best help the organization," Mr. Cork said. "Let them say yes or no."
If lunch seems a stretch, suggest coffee. If it's a go, it's best to get out of the office, because it keeps the discussion informal and as private as possible. Also, others can't gossip, he said.
THROW YOUR BEST PITCH
"Don't get caught in the trap of thinking informal means unprepared," cautions Karen Kelloway, executive coach and consultant with Knightsbridge Robertson Surrette in Halifax and author of a career advice book, Nail It. "Prepare by coming up with a question about one or two key areas that you'd sincerely like to more fully understand. At the same time, ask yourself what value you can provide the boss in the conversation," she said.
One dependable line of questions is simply to ask how you are doing and whether there anything else you need to be doing." The question should be open-ended, such as: "Are there things you could suggest I can do to help you and make your life easier at work?'" Mr. Cork said. Ask about priorities.
BE A KEEN LISTENER
Remember, you are there to learn - not to gripe. "There's much more power in listening and you'll come across as someone serious about knowing the boss' priorities, and who is keen on advancement," Ms. Kelloway said.
GET PERSONAL
Connecting on your boss's interests is the best way to reduce barriers between the two of you, Mr. Cork said. "This is also an opportunity to find out more about how they spend their time away from work, about their families and other things that drive and motivate them. Take mental notes and jot down the information afterwards," he said. "If you can ask in the future how son Bobby or wife Sherry is doing, it will score bonus points because it shows you have listened and connected."
AVOID BOOBY TRAPS
Steer away from areas you don't know about or you sense may be too sensitive, Mr. Cork said. For example, if the boss's passion is golf or soccer and you don't really know the sport, getting into a discussion will make you sound insincere. And don't push for details if they aren't forthcoming.
OFFER AN INITIATIVE
It's best to come away from the meeting with an action item that will demonstrate your enthusiasm and give you a reason to follow up, Ms. Kelloway said. "Create an innovative project, or offer to help develop strategies to fix a nagging problem that everyone recognizes is a problem, but no one has been willing to tackle," she said.
"If the talk turns to the company being interested in ways to cut its environmental impact, you could suggest something like: 'Since it's a bit slower during the summer, would you be interested in letting me develop some strategies to do this?' This will demonstrate not only your commitment, but also your aspiration to take on a more senior role," Ms. Graham said.
THE FOLLOW-UP
It you make the effort to get to know your manager better, you're likely to find he or she welcomes the opportunity to hear your perspective.
Mr. Kincaid, of Level5, certainly does. "I appreciate the discussion and the candour and feedback I've had with employees in these informal discussions out of the office," he said. "We can talk more matter-of-factly and ask tougher questions than we can in the workplace."
After his out-of-office discussion with Mr. Wise, Mr. Kincaid decided to aside an evening each month to have what have become known in the company as "Dates with Dave."
So many employees are ready to buy him a beer, that they have to put their names in a hat for a draw to see who gets the next night out. Mr. Kincaid said he is looking forward to some spirited discussions. "I like it when they test me and challenge decisions. That's how we all learn to get better."