[Aligning with the CEO] Hi, not sure how to phrase things (or maybe im asking the wrong questions), but i’ll it anyway to at least get the conversation started. [Short Story] April 2, CEO called me into his office and said to expedite and issue that we’ve been tackling for about 2 months now. I thought we were in a good pace but I guess I was wrong. That’s on me. Then we came up with a plan to find an outsourcing team and to outsource it. We executed the plan, constant communication and updates, we stayed nimble to the plan, picked two outsourcing teams from our selection of 4, started working on the project, then CEO changed his mind, overrode my recommendations and said to go with 1 of the 4 outsourcing vendors (that did not make the cut). So to me, how do I address this misalignment? How do I get the CEO’s “trust” so that I can start managing the technical risks instead of him managing it himself (he’s not techy btw)? [LONG Story] I just joined as the CTO of a 2yr old startup that has been doing a lot of things manually before i joined. I’ve been in the company for 2.5mos now and hiring devs have been difficult that we dont have much right now. The CEO all of the sudden became frustrated with one of our manual to automation activity. I was working on it (myself) but was only having slow and incremental victories (because Im just one man). So we decided to go for outsourcing. At this point in time, it was April 2 and our CEO wanted it done by end of April. What our CEO prefers is we outsource the work for X months, then we absorb those people after said duration. That way we can address our resourcing issue as well instead of going back to a thin team after the outsourcing. I told our CEO that I dont know of anybody that does that but he said our COO does. I said ok, i’ll see what I can do. We decided to pick the outsourcing company April 4. Also as a context, the system that I inherited came from another external company. It’s not that bad but it does need some work. Plus, it was written in a language and framework that’s not so mainstream (so people with that skillset are harder to find). So our COO got 2 outsourcing companies C1 and C1. Only C2 was able to provide that absorption model. I brought in C3 and C4. They dont offer absorption but they do provide the exact skills that we need and can provide it immediately. Come April 4, C1 is out, C2 has no proposals yet, C3 and C4 already have already given theirs. COO said to move the decision making on the 5th to give C2 chance. April 5th (friday) came and still nothing so moved it to April 8th (monday). April 8th came, CTO of C2 came, I talk to him (both CEO and COO were out), figured out that they didnt have the resources we need, so I said we’ll just contact them for future possible outsourcing. April 9 came, i told them we need to make a decision because we’re losing days, had a long phone conversation with our CEO, we decided to get both C3 and C4. April 10 came, CEO and COO were both back in the office, CEO raised a lot of issues because he still does not understand how we’re going to address the april timeline and the actual resourcing of the dev team with staff augmentation. I explained that staff augmentation will address the immediate concerns but we need to keep doing recruitment. And i told him HR and I are trying something different to address that issue already as well. (CEO is not techy btw). He also asked about the plans for our system because it’s hard to find resources for it. I told him we need to stay in that system for now, hire people that may not have those skillsets and just train them, and then we break that monolith into microservices so that we can start moving away from that legacy tech. But for now, if we want to address immediate concerns safely, we need to work on the monolith until we have a better understanding of how its pieces work. There were a lot of other questions but I do hear our CEO saying “now i understand”. So i thought it was a win Also by April 10, C3 and C4 already got access to the source code and some documentation. April 12, I already oriented them about the Sprint stories and had some initial guesstimates. April 15 (monday) came and C3 and C4 started full throttle working on the stories. April 16 (tuesday), our CEO requested for a “2 minute” meeting with me. I came in, and he said, he gave it a lot of thought during the weekend, and talked to 3 other CTOs and he said we’re going with outsourcing C2. I told but C3 and C4 already started. He said he thought i was waiting on him to sign the papers. I told him with that deadline we have, i cant wait for such things. But anyway, i told him why C2? He said from what he knows, C2 can provide people immediately, not the skillsets that we need, but they can retool themselves, then deliver by end of April. I told him, I dont think that’s possible. April 16 night, i met up with C2 again, tried to check their plans, and indeed, they wont be able to pull it off. We have 4 guys from C3 and C4 with the skillset that we need. C2 on the other hand will give us 1 guy that would spend a week studying our tech. Even if he is going to break things into a microservice so that he can work on the tech that he’s familiar with, he still need to be able to be knowledgeable enough on the legacy system’s domain design, architecture and technology to be able to surgically remove a piece as a microservice (and there are no tests on the legacy system). To be fair, i did not push or pressure C2 to figure out a way to deliver by end of April. Because to me, that’s unrealistic. So I sent an email that night to our CEO telling him we can go with C2 but we miss the end of April deadline. And he said, he’ll talk to the CEO of C2 directly and will update me. And I told him if C2 can figure out to deliver by end of April, then that’s great. But it needs to be a sound plan. *no news yet* - Pulse Q&A

[Aligning with the CEO] Hi, not sure how to phrase things (or maybe im asking the wrong questions), but i’ll it anyway to at least get the conversation started. [Short Story] April 2, CEO called me into his office and said to expedite and issue that we’ve been tackling for about 2 months now. I thought we were in a good pace but I guess I was wrong. That’s on me. Then we came up with a plan to find an outsourcing team and to outsource it. We executed the plan, constant communication and updates, we stayed nimble to the plan, picked two outsourcing teams from our selection of 4, started working on the project, then CEO changed his mind, overrode my recommendations and said to go with 1 of the 4 outsourcing vendors (that did not make the cut). So to me, how do I address this misalignment? How do I get the CEO’s “trust” so that I can start managing the technical risks instead of him managing it himself (he’s not techy btw)? [LONG Story] I just joined as the CTO of a 2yr old startup that has been doing a lot of things manually before i joined. I’ve been in the company for 2.5mos now and hiring devs have been difficult that we dont have much right now. The CEO all of the sudden became frustrated with one of our manual to automation activity. I was working on it (myself) but was only having slow and incremental victories (because Im just one man). So we decided to go for outsourcing. At this point in time, it was April 2 and our CEO wanted it done by end of April. What our CEO prefers is we outsource the work for X months, then we absorb those people after said duration. That way we can address our resourcing issue as well instead of going back to a thin team after the outsourcing. I told our CEO that I dont know of anybody that does that but he said our COO does. I said ok, i’ll see what I can do. We decided to pick the outsourcing company April 4. Also as a context, the system that I inherited came from another external company. It’s not that bad but it does need some work. Plus, it was written in a language and framework that’s not so mainstream (so people with that skillset are harder to find). So our COO got 2 outsourcing companies C1 and C1. Only C2 was able to provide that absorption model. I brought in C3 and C4. They dont offer absorption but they do provide the exact skills that we need and can provide it immediately. Come April 4, C1 is out, C2 has no proposals yet, C3 and C4 already have already given theirs. COO said to move the decision making on the 5th to give C2 chance. April 5th (friday) came and still nothing so moved it to April 8th (monday). April 8th came, CTO of C2 came, I talk to him (both CEO and COO were out), figured out that they didnt have the resources we need, so I said we’ll just contact them for future possible outsourcing. April 9 came, i told them we need to make a decision because we’re losing days, had a long phone conversation with our CEO, we decided to get both C3 and C4. April 10 came, CEO and COO were both back in the office, CEO raised a lot of issues because he still does not understand how we’re going to address the april timeline and the actual resourcing of the dev team with staff augmentation. I explained that staff augmentation will address the immediate concerns but we need to keep doing recruitment. And i told him HR and I are trying something different to address that issue already as well. (CEO is not techy btw). He also asked about the plans for our system because it’s hard to find resources for it. I told him we need to stay in that system for now, hire people that may not have those skillsets and just train them, and then we break that monolith into microservices so that we can start moving away from that legacy tech. But for now, if we want to address immediate concerns safely, we need to work on the monolith until we have a better understanding of how its pieces work. There were a lot of other questions but I do hear our CEO saying “now i understand”. So i thought it was a win Also by April 10, C3 and C4 already got access to the source code and some documentation. April 12, I already oriented them about the Sprint stories and had some initial guesstimates. April 15 (monday) came and C3 and C4 started full throttle working on the stories. April 16 (tuesday), our CEO requested for a “2 minute” meeting with me. I came in, and he said, he gave it a lot of thought during the weekend, and talked to 3 other CTOs and he said we’re going with outsourcing C2. I told but C3 and C4 already started. He said he thought i was waiting on him to sign the papers. I told him with that deadline we have, i cant wait for such things. But anyway, i told him why C2? He said from what he knows, C2 can provide people immediately, not the skillsets that we need, but they can retool themselves, then deliver by end of April. I told him, I dont think that’s possible. April 16 night, i met up with C2 again, tried to check their plans, and indeed, they wont be able to pull it off. We have 4 guys from C3 and C4 with the skillset that we need. C2 on the other hand will give us 1 guy that would spend a week studying our tech. Even if he is going to break things into a microservice so that he can work on the tech that he’s familiar with, he still need to be able to be knowledgeable enough on the legacy system’s domain design, architecture and technology to be able to surgically remove a piece as a microservice (and there are no tests on the legacy system). To be fair, i did not push or pressure C2 to figure out a way to deliver by end of April. Because to me, that’s unrealistic. So I sent an email that night to our CEO telling him we can go with C2 but we miss the end of April deadline. And he said, he’ll talk to the CEO of C2 directly and will update me. And I told him if C2 can figure out to deliver by end of April, then that’s great. But it needs to be a sound plan. *no news yet*

@IT Number of answers: 0

Douglas Ljung, Director of Information Security

, answered on 2019-04-24T00:35:05.436Z, a month ago

Without knowing all the details and personalities I offer you my opinion. The CEO and CTO are so used to successfully handling the issues themselves as a startup, before you arrived, that they continue to do so out of habit/fear. You should tell them tomorrow that this particular outsourcing project would be a solid opportunity for you to prove yourself to them. If they agree, then tell them to leave you to it (sounds like you are committed to outsourcing with a particular vendor already) and you will create a detailed/realistic plan with deadlines and deliverables. If they don’t agree, then your chance for this to be your official trial by fire may have passed. You can then tell them that you will support them in this effort but would appreciate the opportunity to handle the next grand event on your own. Having someone change the roadmap, especially over the weekend, is frustrating, confusing, and shows a lack of delegation. I’ve called my leadership out on this and they either really want to project (perhaps they did it before) or most often are relieved that someone wants take it off of their shoulders so they can focus on other important fires.

upvotes: 1

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[Aligning with the CEO] Hi, not sure how to phrase things (or maybe im asking the wrong questions), but i’ll it anyway to at least get the conversation started. [Short Story] April 2, CEO called me into his office and said to expedite and issue that we’ve been tackling for about 2 months now. I thought we were in a good pace but I guess I was wrong. That’s on me. Then we came up with a plan to find an outsourcing team and to outsource it. We executed the plan, constant communication and updates, we stayed nimble to the plan, picked two outsourcing teams from our selection of 4, started working on the project, then CEO changed his mind, overrode my recommendations and said to go with 1 of the 4 outsourcing vendors (that did not make the cut). So to me, how do I address this misalignment? How do I get the CEO’s “trust” so that I can start managing the technical risks instead of him managing it himself (he’s not techy btw)? [LONG Story] I just joined as the CTO of a 2yr old startup that has been doing a lot of things manually before i joined. I’ve been in the company for 2.5mos now and hiring devs have been difficult that we dont have much right now. The CEO all of the sudden became frustrated with one of our manual to automation activity. I was working on it (myself) but was only having slow and incremental victories (because Im just one man). So we decided to go for outsourcing. At this point in time, it was April 2 and our CEO wanted it done by end of April. What our CEO prefers is we outsource the work for X months, then we absorb those people after said duration. That way we can address our resourcing issue as well instead of going back to a thin team after the outsourcing. I told our CEO that I dont know of anybody that does that but he said our COO does. I said ok, i’ll see what I can do. We decided to pick the outsourcing company April 4. Also as a context, the system that I inherited came from another external company. It’s not that bad but it does need some work. Plus, it was written in a language and framework that’s not so mainstream (so people with that skillset are harder to find). So our COO got 2 outsourcing companies C1 and C1. Only C2 was able to provide that absorption model. I brought in C3 and C4. They dont offer absorption but they do provide the exact skills that we need and can provide it immediately. Come April 4, C1 is out, C2 has no proposals yet, C3 and C4 already have already given theirs. COO said to move the decision making on the 5th to give C2 chance. April 5th (friday) came and still nothing so moved it to April 8th (monday). April 8th came, CTO of C2 came, I talk to him (both CEO and COO were out), figured out that they didnt have the resources we need, so I said we’ll just contact them for future possible outsourcing. April 9 came, i told them we need to make a decision because we’re losing days, had a long phone conversation with our CEO, we decided to get both C3 and C4. April 10 came, CEO and COO were both back in the office, CEO raised a lot of issues because he still does not understand how we’re going to address the april timeline and the actual resourcing of the dev team with staff augmentation. I explained that staff augmentation will address the immediate concerns but we need to keep doing recruitment. And i told him HR and I are trying something different to address that issue already as well. (CEO is not techy btw). He also asked about the plans for our system because it’s hard to find resources for it. I told him we need to stay in that system for now, hire people that may not have those skillsets and just train them, and then we break that monolith into microservices so that we can start moving away from that legacy tech. But for now, if we want to address immediate concerns safely, we need to work on the monolith until we have a better understanding of how its pieces work. There were a lot of other questions but I do hear our CEO saying “now i understand”. So i thought it was a win Also by April 10, C3 and C4 already got access to the source code and some documentation. April 12, I already oriented them about the Sprint stories and had some initial guesstimates. April 15 (monday) came and C3 and C4 started full throttle working on the stories. April 16 (tuesday), our CEO requested for a “2 minute” meeting with me. I came in, and he said, he gave it a lot of thought during the weekend, and talked to 3 other CTOs and he said we’re going with outsourcing C2. I told but C3 and C4 already started. He said he thought i was waiting on him to sign the papers. I told him with that deadline we have, i cant wait for such things. But anyway, i told him why C2? He said from what he knows, C2 can provide people immediately, not the skillsets that we need, but they can retool themselves, then deliver by end of April. I told him, I dont think that’s possible. April 16 night, i met up with C2 again, tried to check their plans, and indeed, they wont be able to pull it off. We have 4 guys from C3 and C4 with the skillset that we need. C2 on the other hand will give us 1 guy that would spend a week studying our tech. Even if he is going to break things into a microservice so that he can work on the tech that he’s familiar with, he still need to be able to be knowledgeable enough on the legacy system’s domain design, architecture and technology to be able to surgically remove a piece as a microservice (and there are no tests on the legacy system). To be fair, i did not push or pressure C2 to figure out a way to deliver by end of April. Because to me, that’s unrealistic. So I sent an email that night to our CEO telling him we can go with C2 but we miss the end of April deadline. And he said, he’ll talk to the CEO of C2 directly and will update me. And I told him if C2 can figure out to deliver by end of April, then that’s great. But it needs to be a sound plan. *no news yet* - Pulse Q&A

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