It starts with a winning attitude
Raptors GM Bobby Webster dips into the Mailbag. Don’t worry, he’s keeping his day job
We’ve given over this space this week to Raptors general manager Bobby Webster to give him a chance to answer questions directly from Star readers. His time and insight and greatly appreciated. Take it away, Bobby …
Thank you to everyone for submitting your questions and thanks to Doug for allowing me a quick spin in his world. It takes a lot of time to read through all of the questions and thoughtfully respond so I don’t think I’ll be making a career change anytime soon, Doug! Unfortunately, I didn’t have time to answer all of your questions, but this gives us an excuse to do it again!
We always hear about culture but exactly what is the culture of the Raptors and how would you define it? How does this play into the players that you draft, trade for or sign as free agents, or even the hiring of employees? How much does being competitive and having a winning attitude fit in with this?
— Edward
Great question, Edward. It’s something that we are always trying to get better at, something we’re very aware of … who we are as an organization, how do our staff and players feel about that, are they constantly growing within their current roles? A few words come to mind when we talk about the culture of the Raptors. First and foremost, what you said, winning and being competitive. Do they work hard? Are they selfless? Does the team come first? Are they physically tough? Are they mentally tough? These are all very general characteristics that we look at and I think anyone can appreciate that it takes an entire team, an entire organization working toward the same goal to actually accomplish it.
There are little things that can get you off track. Maybe individual goals or personal relationships or maybe someone’s just having a bad day — and those are all things you have to overcome along the long journey — but as long as you have the types of players, the types of staff, the types of coaches who value the same things that you do, it does make it a little bit easier.
I’d be curious what the Raptors use for their future roster-planning window. Two years is too short but is five too long? Do you have baseball-style, roster-depth planning and how many years is appropriate in basketball? — Blair
The easy answer is we don’t use a window, we don’t have a one- or two- or three-year window. The easiest way to think about it is we have shortterm and long-term planning and both of those time periods are kind of irrelevant.
Short-term planning is as the playoffs approach: Do we have enough depth at each position? Are players injured? Do we need a specific type of insurance, specific role as we enter the playoffs? Do we need more ballhandling help? Do we need more shooting? Those are all kind of short-term needs.
The long-term needs are probably what gets talked about a ton: What are you going to do this summer? How are you going to approach the draft? How are you going to approach free agency? Those things aren’t always at odds, but they can be and I think one of the really tough parts of the job is balancing the win-now approach (and putting) together a team that could potentially contend for a championship for multiple years?
I think hopefully people have seen over the years, we’ve tried to limit our long-term commitments not because we don’t believe in some of those decisions but it just maintains our flexibility. It’s really hard to predict the future as everyone knows. Look what we’re going through right now. So to have the flexibility, to have the ability to pivot and to make different decisions every season or off-season is important to us because we’re constantly evaluating the team.
Besides some of the obvious highlights of playing for the Raptors (i.e. country, fan base, winning), what smaller, but in your opinion, very significant qualities would you highlight to a free agent considering the team? — Nathan
I think the first one, and I don’t want to gloss over it, is the winning. It’s always first, it’s foremost in any presentation that we give or any meeting that we have with a free agent. It’s something that we’re proud of, what we built here and are trying to sustain.
Obviously the expectation to win comes along with that and that presents its own challenges and motivations but that’s always been our goal, to attract players that care about winning because we do.
The next one is our ownership group and MLSE. They are in a position to provide us with all of the resources we need and that kind of shows itself: the Raptors 905, our G League team in Mississauga, which is really important for the development of our players and staff; our practice facility; the staff that we’re able to hire, to put literally the best staff in the NBA around these guys.
And it’s not a given. I’ve been around the league a bit and it’s not a given that you have that type of support above you. I think the players feel it, I think hopefully the city, the country and our fans feel that we’re all on the same page and that we’re in it together. I think it’s really important to get that sense from ownership in order to achieve what you want to.
My son Ethan, aged nine, is interested in your career path. Do you have plans for a different role after being a GM? — Katie
Ethan, you’re ahead of your time thinking about your future GM career. I grew up loving basketball from as young as I can remember, but didn’t realize all of the jobs that went into creating an NBA game until I graduated from college. Whether you watch a game on TV or in the arena, there are so many different roles — you can play, coach, sell popcorn, take videos or photos, dance, scout, etc.
Like many first jobs, I started right out of college as an intern, and I was lucky enough for it to be in the NBA with the Orlando Magic. I don’t really remember exactly what I did, but the most important part was simply doing a great job in whatever I was asked to do — staying late to make the last FedEx delivery, driving visitors around town, helping my boss move houses, and sometimes it was even fun stuff, like playing basketball whenever the CEO flew into town. Thinking back, I was trying to be as helpful and thoughtful to everyone I worked with, but at the same time I was also listening and observing everyone and everything to learn about the business.
From Orlando, I moved to New York where I worked for seven years at the NBA offices. I continued to grow and mature as a person, while learning even more about the NBA and how it operates. Masai (Ujiri) called me seven years ago to come work for the Raptors and the rest is history! Time flies, and I’ve been incredibly fortunate to receive a lot of good advice over the years.
When you’re looking for your first job, figure out what you love to do and find the best organization that does it. You’ll end up surrounded by people just like you, young, energetic, full of aspirations and ambition. And if you’re really lucky, you may never have to leave or look for another job the rest of your career. As much as you’ll want to work 24/7, don’t forget to grow as a person, find new friends and experiences. Being well-versed with people from all backgrounds and walks of life will take you far. What effect will the curtailment of all basketball have on your draft preparations? How will you evaluate prospects and do you already have a list? — James Similarly to everyone else in the world, we’re all learning how to work from home and adapt to our new surroundings. Whether it’s preparing for the draft, continuing the season, or free agency, the biggest thing that stands out to me is how innovative we all are when faced with adversity and new challenges. We’re figuring out new ways to communicate with draft prospects online, we’re imagining a new NBA with more fans watching from home, and rethinking how Toronto and Canada can be a unique destination for future Raptors players.
It’s incredible to see how we’re all staying connected and thriving in ways we’re never thought possible. We all fall into cycles of doing the same thing the same way, but when we’re forced to think about things from a new angle, we end up talking to family and friends that we haven’t seen in years, discovering new recipes to cook at home, and slowing down our pace of life to better absorb what’s going on around us. I’m looking forward to seeing what sticks with all of us in the future.
Read more on Doug Smith’s Sports Blog at thestar.com and send your questions to askdoug@thestar.ca. We reserve the right to edit for length, clarity and punctuation.