(390) Proven Methods for Coaching AEs to Master Discovery and Close More Deals (Sean Gentry, WebFlow) - YouTube https://www.youtube.com/watch?v=yI6N80IFdfg

Transcript: (00:00) [Music] good morning everybody and welcome to this leadership episode of 30 minutes to president's Club my name is Arman fro and I'm here with my co-host Nick seeli we have a round two with the guy who comes from two of the baddest coaching family trees you could imagine coached by both Mark coslo Kevin dorsy it is the one and only sha Gentry for round two and holy smokes is it obvious that this guy has become a sales leader from the best is a senior manager of corporate sales at webflow Nick why should people (00:36) listen Sean has some really practical things in terms of coaching reps to look out for risk and friction in deals and he's got some extremely regimented particular ways that he pulls that out from reps in multiple different places in how he works with them everything from how he has the manage the CRM and the data that's in there and the format of it to how he's role playing on one-on ones to question that he is asking by stage of deals in pipe reviews and so this was a really really good one if you are looking to help improve the way that (01:08) you work with your reps and 3 2 1 Let's Roll Sean back to the show we start every leadership show with your top three actionable takeaways let's get your three all right first I've got the CYS this is the call your shot meeting so every single Monday morning I tap one of my reps to tea up it's a peer Le meeting instead of me just you know spitting some housekeeping facts about the company they are going to tap every single one of their peer AES to call their shot for that week so whether it's you know book two meetings with the new prospects (01:39) whether it's to find five new outbound accounts whether it's you know getting that CFO on that value pricing call on Thursday they're calling their shot we're checking in midweek and then on our team meeting on Friday we're getting together to se celebrate those incremental wins to stack them up month over month quarter over quarter to help them improve get their number boom what's number two all right so number two is the ptq it's the path to quota so in my last two shops Outreach and web flow the top performers have always (02:09) known their path to quota so they enter every single quarter with what they have in their pipeline it's normally colorcoded red yellow green they've got to commit most likely best case they understand the risk and then they shoot for a pipeline goal whether that's 3.5 or 4X and then through the month they're tracking essentially their path to quotas what do they have closed one what is their quota what do they pay faing towards what do they need to create in their pipeline to get back to that Forex number and they're keeping track of this (02:36) every single week so that in our one-on ones when we meet we can make sure are they on Pace are they on target are they behind pttt path to takeaway I love it it's the full acronym episode this is the ncwf this is my favorite acronym it's no commission without friction so every single deal is going to have friction I don't care how smooth that's running you're going to hit friction around pricing around Red Lines around procurement around involving a different department maybe you're going to get three or four sea level execs to have (03:09) eyes on this proposal there's going to be friction no deal is that smooth so going into every single one-on-one deal inspection review when I'm talking to my reps that is my first question where are you hitting friction if you haven't already it gets them in the mindset to see that potential risk is coming and then train them to get ahead of it every single time so talk to me about what that conversation looks like you're on a one-on-one or you're on a pipe review with your rep and you're talking about a deal what are some of the common areas (03:39) and you can use web flow you could use Outreach you mentioned like pricing you mentioned oh we need to get other departments involved what are some of some of the common areas you will Coach them to look for friction or risk in the deal yeah I think one of the things that's interesting about a SAS market now especially compared to you know a couple years ago if I take Outreach for example pre-co Outreach was selling a sales product to sales people that's what it was geared for now with all the different products and multi-services (04:05) that they offer sales has eyes on it but it's also being used by customer success it's being used by marketing right and now to be a successful SAS product they have to be multipronged in their approach and so inevitably when I'm working with one of my reps and they're only targeting or working with one Department that's what I'm asking them like does engineering Have Eyes on this does their security team or their legal team Have Eyes on this yet because that's where friction is going to occur right if you don't have multiple people (04:32) involved in this or part of that decision-making process when that proposal hits their desk and they don't know anything about the product or the problems that we solve friction is going to occur so in webflow specifically like we are very marketing heavy we work with a lot of VP CMOS and marketing but if we don't have engineering as a part of that conversation even halfway through on a demo or technical evaluation I know that we're going to hit friction towards the end usually I'm always curious with the rep is this an initiative that was (04:59) brought on due to like an executive measure within the business where multiple departments are aware of it or is this something that let's say marketing has sought to look out for themselves because of a problem they have and it's siloed and then they're going to bring it to the business at the end go seek out this product and you know bring me the pricing quote it's rarely the you know it's rarely that case and more often the latter where marketing's got a problem they find it out and then they take it to the CEO to (05:25) present towards the end so when I'm working with my rep I always want to understand like where are they in the process in terms of who is involved or who's aware of this but if engineering is not involved which we know is a big factor in determining like a website shift right and and who's going to be doing a lot of this resourcing then I'm tasking my reps to pull up those people in engineering on LinkedIn on Zoom info and approaching the people in marketing with hey is Carol part of this decision is Jessica involved in this are they (05:53) aware of this are they experiencing any of the flak that you're seeing in marketing what does that relationship look like because if they don't have some of those answers right now it's on us to proactively approach our buyers with that and get past that hurdle sooner than later like we want to get ahead of that potential objection because I've been there in that seat you know towards the end where we present that proposal and come back and say oh engineering doesn't want to change their workflow we're going to stick with (06:19) status quo you talk about this engineering risk in a deal my guess is at different stages of a deal there are different common risks and and in your head you probably have 30 or 40 blind spots that could be happening in any given deal how do you know which ones to point out to your reps at what times yeah I think a lot of it comes to exit criteria for the deal itself like you want to know on a general sense whether it's Discovery or demo what the rep should know or be walking away with you know if you go on LinkedIn now you see (06:50) people talking about multi-threading all the time it's a huge aspect and you need strong multi-threading to get deals through in this climate but it's hard to sell other departments if the people you're talking to aren't sold right and so one of the things that normally is best in my opinion is if you're working through like Discovery and demo and I'm let's say I'm working with a marketing department I need to ensure that not only do we solve their problem but they believe that we are the vendor of choice before they start looping in other (07:19) departments and so through that I imagine it as if we're sitting on two opposite sides of the table right if I'm on I'm selling to you we're sitting on opposite sides of the table and I finally get to demo you I get to go through technical evaluation and I ask you that question of hey if this was solely up to you pricing aside do you believe that we're the right fit moving forward do you believe this is a partnership that you would buy and if you give me anything other than a resounding yes I need to backup right I (07:45) need to figure out what I missed or why we aren't aligned but if you say yes Sean this is awesome I love this it's like you kind of moved your seat to the other side of the table and we're sitting together and now your whole company opens up and I get to ask you like hey I know Jessica from engineering they normally work with marketing on the website how does Carol think about this your CMO and I'm using you as that champion that guide to kind of help me to quarterback me basically through the company and get to the next people but I (08:14) need you sold first that's the key right there is the risks are the risks associated with achieving the exit criteria for that stage so oftentimes managers will actually try to drisk everything that could happen in a deal in the next four stages but to your point if you're in the discovery stage do you have a real problem with a real champion and most of your questions are around that but if you're in the multi-threading phase the questions you're going to be asking are are you having all the right people involved or (08:46) does power really give a damn about that problem so all you have to do is just up figure out have a list of common things that blow up deals in this stage and put those in public forum for your reps and ask them questions about it I want to ask you about deal reviews because Arman you just talked about from the the sales leaders perspective like hey here's the questions you should be asking risks associated with Stage Sean when you're working with new reps who come on your team who might not have worked with you (09:14) before how do you teach them to talk about their deals what are the things that you tell them they need to be looking out for and communicating up to you because my guess is you're not saying share every single last detail from like oh this person also has a lake house in Wisconsin and they're really in like I imagine you're giving them some coaching in terms of what you want them to be communicating and how they communicated to you I think part of like setting the expectations up front is huge from a leader especially going into (09:41) these one-on-ones and how you're going to not only inspect the deals but how you're going to coach them and the key things that I tell every single one of my reps is that showing up to let's say a forecast or Deal review they have to have their Pipeline and Salesforce clean and up to dat it's just a set expectation for me that if things are not dialed and up to date I'll cancel the meeting or reschedule it because I don't want to spend the 30 or 45 minutes I have with my reps going through and doing housekeeping under deals so I (10:09) would say like Hey we're going to push this meeting to tomorrow when we show up tomorrow I want everything clean and what that actually means is I want the ARR and close dates up to date but most importantly my next step Fields I'm very particular with my reps and they need a couple things in every single thing number one is the date that the the next step is being entered so today let's say it' be you know July 24th that's the first thing and then the next thing is it needs to have their tactical next step and I think this is the biggest (10:40) difference and where most either sales managers or most AES miss the boat is that more often than not it's a status update right waiting for Bob to return the contract is not a Next Step Right Carol's gon to get back to me with times that's not a next step that's a story right that's a status update so I want to know what my rep is doing next if they're waiting for Bob to get the contract to them are they calling Bob at Wednesday at 3 p.m. (11:06) to ensure that everything is signed right so what is their exact Next Step so when I go into every single forecast review I can look at you know super Biz is the first title let's say the first deal they're working and I go through very quickly to say hey Nick it looks like you've got super Biz forecasted for July 31st at $50,000 are those things still accurate and you can say yes they are and I Sayre it looks like your next step is is to call Bob at 300 p.m. (11:33) to ensure he's got the docu sign in hand and the goal is to get that signed by Thursday morning let's prepare for if Bob doesn't answer what is your next step right do you have what I believe to be the right Next Step or can we game plan if that goes sideways or is there risk involved and so it's really setting the expectation with the rep and then having basically like a format that you can go through with every single one of your reps to ensure that you were doing it the right way and then they're doing it the right way leaders today are (12:01) terrified to do things like ask their rep to make a certain number of dials every week or ask people to update Salesforce and keep their pipeline up to date so that we don't talk about have you talked to this opportunity in the last seven months and instead we just talk about great let's talk about how to drive these deals forward the reason you keep pipeline clean is so you don't have to waste time talking to each other about pipeline janitorial exercises and so Sean you have a clean pipeline all the next step are up to date you have (12:30) all the dates of the next actions what the goal is how do you decide which deals you're going to dig into yeah so every single time I start a forecast review I start with the highest ARR activity or opportunity first every single time so I don't care if you have you know super Biz let's say and it's $150,000 but it's slated to close in January what happens more often than not is that managers only focus about what's in front of them so they'll focus on the July deals the August deals the September deals and you've got this huge (12:59) opportunity let's say can hit your entire number in one deal but it's slated for January it either gets not brought up into the filtered view of Salesforce or Clary whatever you use or you're simply not going to talk about it and I believe that deals don't necessarily die due to timing they do to lack of momentum right and so even if you have this deal that's out in January what is the rep doing to continue to nurture to drive other people into the conversations and we're going to talk about that at the top of every meeting (13:27) right so even if it is slated for January AR and let's say we're focused on ending you know July strong you still got super bid slated for January it looks like your next step is that in two weeks you're sending Carol this new information about a product we're launching and hoping to get a response is that still accurate great it can take 10 seconds but then we're topping on the top ARR activities every single time so that we're going to get to the July deals the August deals as they're filtered in there but I want to make (13:54) sure that we're continuing to drive momentum with the deal that's going to make the biggest Headway for our company Sean one thing that I struggled with a lot was if a deal made it to proposal phase there wasn't a lot to talk about like I knew if we got it there past multi-threading most of my reps knew what to do the hardest part was actually inspecting the top of funnel deals the stage one and the stage two deals because that's where most deals are lost most deals are lost when you can't find a problem in the first place and the (14:26) Reps who are good are the ones who are getting those deals to stages three and four in the first place so if I'm dealing with 20 opportunities in stage one how do I inspect the stage one opportunities without literally going through every single meeting my reps have had one by one yeah so in in stage one stage two like whether it's prediscovery or call it post-discovery I'm always doing initial research like I want to do a quick pulse check if let's say my rep gets a brand new account I'm always quick to check out what (14:59) competitor are they on are they on WordPress are they on contentful are they on sitecore who are they using who are we talking to are we talking to the right Persona that fits into our normal use case and then what size of company it's also crucial for us like I work in the corporate space our reps work 200 to 2 200 accounts but our bread and butter is between 200 and a, that's where we close the most deals so if I get somebody that's 300 employees I'm already starting to think about different levels of risk than somebody (15:25) that's at a 600 employee count so that's part of the pre research that I'm making sure that my reps do postc Discovery and you already mentioned it I want to know really three things number one is do we know that they have a problem that's usually pretty easy for an AE who's doing this all the time to sus out the number two one is do they know how they have a problem right have they admitted they have a problem which inbound you're going to get much easier than an outbound activity and then the third thing is are they willing to go on a (15:56) journey with us to solve it and that usually is the biggest kicker that we'll get through a proposal and our AES will say like oh I know they have this problem but if they're not willing to go on the journey with us to solve it we're screwed we're not going to get that deal signed and so coming out of that like exit criteria out of Discovery phase I want to know like are they the right fit do they fit our demographic do they fit the use case do they fit the type of company and then do they actually acknowledge they have a (16:23) problem and they want to solve it this is a really interesting framework you have which is like do we go into the call with our understanding of like we think they have this problem it almost feels like you're going in with a POV and you're trying to get them to admit to or reveal hey yes this problem exists and often if we go in with the POV even if we're wrong it earns us them sharing the other problem that they might have um you might have a different direction of like how you're coaching the rep either before that Discovery (16:52) call or like how you're teaching them to go through that framework with a customer one thing Nick about that like I so I've been working with with Chris Orab for a while and he he talks about menu based Discovery and like stealing his ex exact words that's like what I'm training my reps on that if you know 99% of the web is built on WordPress we encounter it all the time and so even if I know like hey you've got super Biz it looks like they've got 500 employees on LinkedIn we're talking to a you know a senior director of marketing their (17:22) buildt on WordPress my reps are entering that Discovery with a point of view exactly to say like hey I know this movie I've seen it before this is going to be your first time but I'm going to tell you that normally when I talk to people that are on WordPress they're encountering A and C which one of those resonates the most for you or is it something completely different right so it's it's I'm basically like outlining what pain you're going to have you're going to either choose one of those things or say hey no either I'm not and (17:51) then we're not potentially they not the right fit or not ready or they're going to say oh yeah I'm really struggling with a and then it's like great what's the pain behind the pain and then can you admit that and like do you actually want to solve it so teaching Discovery is extremely challenging it can go in so many directions it's this massive if this then that equation and you cannot script every direction so let's start with the menu of pain you have two or three common problems you might solve based on these different situations once (18:21) your reps present those problems how do you coach them to take the call forward from I think a lot of it is working backwards like we know where we eventually want to get in Discovery and it's for them to admit that they have a problem that needs to be solved if if you think that that's the end goal is the end part of the movie and like what is the third act second act First Act that gets you there and what's unique about webflow versus a company like I I worked for outreach for a long time is that Outreach we knew exactly what (18:48) product we sold who we sold it to and what problems we solve and we could do it it you know you called me at 2 am and said hey like pitch Outreach I could do it in my sleep the interesting thing about webflow is that that a website can serve so many different purposes it can be a lead generation platform for companies it can be an event page it could be landing pages that they spin up and so the Reps have a very unique and interesting learning curve because they have to learn menu based Discovery for so many different competitive Landscapes (19:18) and competitors out there but if we know like the core principle of Arman you admitting that you have a problem and that you want to find out more to solve it that's the core principle we try to hang our hat on and then if we know that like WordPress we're going to encounter that more than anybody else we know based off the current customers that we've sold why they buy webflow off WordPress and I think that's like I've been talking about this for a long time that I think we need to do better enablement of when you started a company (19:48) you talk to either current customers or you all that's all you get fed is like why people buy because it could be completely different than why marketing thinks people buy but if we're talking to current customers and saying hey I bought because you know WordPress took me too long to make changes or I had to pay a ton of development resources or you know another option my reps can have those three things based off based off their menu they get chosen and then always coaching from us like you can't stop at the first pain you have to (20:17) understand like once they say things are too slow great like so what who is that impacting is it impacting you is it impacting engineering is it impacting you know your design team like where does it stop and then great it's impacting engineering so what and it's digging down deeper and deeper because there will be through the coaching exercises of like discovery that reps will write in their Salesforce notes oh they're on WordPress and it's too slow like part of that is just tells me initially that they either didn't get to (20:49) a second or third level or they're simply not writing good enough notes in Salesforce but that's an opportunity for me as a leader to see that and call that out and to understand and then call them on it and to say like great hey you said it's taking too slow like what does that mean for them what does that mean for their Partners what does it mean for the or the company and getting them to dig a little bit deeper and if they don't have those answers they got to figure it out in the demo because you talked about (21:12) okay they should be talking to customers and understanding in the customers words why they switched off of Wordpress are you actually having your reps when they on board go and talk to a bunch of customers are there specific trainings you're doing how do you actually empower the team with this stuff um yeah it's one of the interesting things about the company culture of web flow I'm sure other companies do this but every time we sign up a new company to to webflow we've got a slack Channel specifically for this of the rep going in and (21:40) outlining who they signed up what they signed up with but more importantly why they signed up and the competitive reasons and so this highlights to the entire company like hey I've signed up 30 minutes to president's Club on webflow and they signed up from WordPress and here's why they signed up and so the nice thing us from from our point of view especially being in slack is that if I'm talking to let's say one of your competitors right and they're looking also at webflow I can type in like okay podcast WordPress and search (22:11) it in slack and I can get several answers of people that have signed up from that platform and why so I can quickly search and have things to talk to what you're talking about is a lot of people over rotate on product training this is the solution that we offer and the first thing that we would always teach at pave is this is why Merit Cycles suck or this is why compensation planning is the worst exercise in the world and if you teach your reps the before state of the infomercial like Josh Brun oftentimes says teach them (22:43) that teach them how to look for that before they even know what your product does you're going to train them to listen for the right types of problems instead of looking for the different places they can just poke a solution in so Sean once they actually understand these problems that they're looking for how did you teach your team how do you actually roll out this discovery framework to your team I think it starts with the any any type of coaching has to start with education or awareness so it's it's about teaching them and then (23:12) showing them and then practicing with them and so if if let's say we're rolling out a brand new discovery framework I'm brand new to this a new company right I think part of it is the awareness like here is what we should be doing and I'm going to show you how it works and then more importantly it's about the pr ractice of let's actually run through it and you know people cringe at the words roleplay but it really is just practicing that day in and day out and I think like looking back at Outreach when I talked about (23:39) answering a phone at 2 am and being able to say it in my sleep it's because we practice it so damn much right and that is like built into me from my Kevin dorsy days at snack nation is that that's all we would do is we would go into rooms before 8 A.M and we would practice over and over and over and over so that by the time we got got on calls it's like we had already gone through the toughest role plays of the day we had already practiced in a ton and so I think with this if whenever you want to roll out a new framework whether it's (24:08) Discovery based demo negotiation is a huge one it's just about showing them or educating how to do it and then it's running through and practicing it over and over are you doing those role plays in group like team sessions like are you doing them in your team meeting or are you doing them on one-on ones with the rep one-on ones yeah I'd much rather do on one-on ones for a couple reasons number one I think it's you know people are always hesitant enough to to practice just in general people always want to save what they're going to do (24:38) and save it for the game right and just be like oh no I watched it I watched a gone call I should be fine on this next one but it's really about getting into that one-on-one and saying hey you have a tough negotiation coming up we know that this cro is going to be tough like let's go through a couple of ways we know we're going to hit friction here around budgets around legal MSA whatever it is and I want to practice through this a couple times with you because also if we're going through one-on-one I feel like it's going to be a little bit (25:06) more comfortable and then also we can just go through it super quick to do four or five iterations in a row of just that section boom Sean amazing round two unfortunately it's not 50 minutes to president's Club it's 30 minutes to president's Club so we have to move to the final question and it is the same what is one bad habit that every sales leader should break so that all sales teams can get a little bit better as any sales leader or anybody that has people below you please stop giving feedback in slack or email this is the tale is Old (25:38) As Time that anything that's written can be misinterpreted right if your partner texts you fine you can read that 50 different ways I listen to a ton of times that I need to get my reps feedback I love the voice feature on slack or simply calling them and giving it to them in direct so always they can hear the inflection in my voice the tone to my voice knowing that I want them to get better I'm in their corner and that's going to do miles for them it's going to be so much better than just you know writing it in a slacker email boom (26:09) all right Nick it is time for a two by two recap from this episode with Sean Gentry what do you have for your two number one you've got to be maniacal about the format of The Next Step field in your CRM Sean makes every deal have the following first the date of the next step second the specific tactical Next Step that is happening in that deal and third the goal of that next step and this makes pipe reviews far more focused on how do we get a successful outcome and less on wait what are you doing next my second is when you are in one-on ones (26:46) with your reps that is the best time to do role plays to prepare for upcoming meetings rather than doing generic role plays in the big team meeting so do them with reps oneon-one number three your framework to evaluate early stage deals is do we know that there's a problem do they know that there's a problem and are they willing to go on a journey with us to solve it and then number four way too often leaders are focused on evaluating the late stage deals so sort your deals by deal size and start with the biggest (27:19) deals first in your pip reviews all righty Nick how could people help us out all right folks if you liked this one with Sean he was actually on this show episode 190 so if you like the stuff you learn from him here go back to episode 190 and give him a listen on that one thanks for listening we'll see you next week on the show [Music]