diff --git a/packages/node/src/executors/package/package.impl.ts b/packages/node/src/executors/package/package.impl.ts
index 0391503fb58d9d..ee6963c2762c8f 100644
--- a/packages/node/src/executors/package/package.impl.ts
+++ b/packages/node/src/executors/package/package.impl.ts
@@ -6,6 +6,7 @@ import {
   checkDependentProjectsHaveBeenBuilt,
   updateBuildableProjectPackageJsonDependencies,
 } from '@nrwl/workspace/src/utilities/buildable-libs-utils';
+import { debounceTime } from 'rxjs/operators';
 import { NodePackageBuilderOptions } from './utils/models';
 import compileTypeScriptFiles from './utils/compile-typescript-files';
 import updatePackageJson from './utils/update-package-json';
@@ -36,16 +37,50 @@ export async function packageExecutor(
     throw new Error();
   }
 
-  const result = await compileTypeScriptFiles(
+  const result = compileTypeScriptFiles(
     normalizedOptions,
     context,
     libRoot,
     dependencies
   );
 
-  await copyAssetFiles(normalizedOptions.files);
+  if (options.watch && 'subscribe' in result) {
+    result.pipe(debounceTime(150)).subscribe(() => {
+      updatePackageAndCopyAssets(
+        normalizedOptions,
+        context,
+        target,
+        dependencies
+      );
+    });
+  } else {
+    updatePackageAndCopyAssets(
+      normalizedOptions,
+      context,
+      target,
+      dependencies
+    );
+  }
+
+  if (options.cli) {
+    addCliWrapper(normalizedOptions, context);
+  }
+
+  return {
+    ...result,
+    outputPath: normalizedOptions.outputPath,
+  };
+}
+
+async function updatePackageAndCopyAssets(
+  options,
+  context,
+  target,
+  dependencies
+) {
+  await copyAssetFiles(options.files);
 
-  updatePackageJson(normalizedOptions, context);
+  updatePackageJson(options, context);
   if (
     dependencies.length > 0 &&
     options.updateBuildableProjectDepsInPackageJson
@@ -57,18 +92,9 @@ export async function packageExecutor(
       context.configurationName,
       target,
       dependencies,
-      normalizedOptions.buildableProjectDepsInPackageJsonType
+      options.buildableProjectDepsInPackageJsonType
     );
   }
-
-  if (options.cli) {
-    addCliWrapper(normalizedOptions, context);
-  }
-
-  return {
-    ...result,
-    outputPath: normalizedOptions.outputPath,
-  };
 }
 
 export default packageExecutor;
diff --git a/packages/workspace/src/utilities/typescript/compilation.ts b/packages/workspace/src/utilities/typescript/compilation.ts
index 71603d0df63f9a..0dd3777f8ea306 100644
--- a/packages/workspace/src/utilities/typescript/compilation.ts
+++ b/packages/workspace/src/utilities/typescript/compilation.ts
@@ -1,5 +1,6 @@
 import { logger } from '@nrwl/devkit';
 import { removeSync } from 'fs-extra';
+import { Observable, Subject } from 'rxjs';
 import * as ts from 'typescript';
 import { readTsConfig } from '../typescript';
 
@@ -13,9 +14,16 @@ export interface TypeScriptCompilationOptions {
   watch?: boolean;
 }
 
+export interface TypescriptWatchChangeEvent {
+  diagnostic: ts.Diagnostic;
+  newLine: string;
+  options: ts.CompilerOptions;
+  errorCount: number;
+}
+
 export function compileTypeScript(
   options: TypeScriptCompilationOptions
-): { success: boolean } | Promise<any> {
+): { success: boolean } | Observable<TypescriptWatchChangeEvent> {
   const normalizedOptions = normalizeOptions(options);
 
   if (normalizedOptions.deleteOutputPath) {
@@ -64,14 +72,20 @@ function createProgram(
   }
 }
 
-function createWatchProgram(tsconfig: ts.ParsedCommandLine): Promise<any> {
+function createWatchProgram(
+  tsconfig: ts.ParsedCommandLine
+): Observable<TypescriptWatchChangeEvent> {
+  const changeSubject = new Subject<TypescriptWatchChangeEvent>();
   const host = ts.createWatchCompilerHost(
     tsconfig.fileNames,
     tsconfig.options,
     ts.sys
   );
+  host.onWatchStatusChange = (diagnostic, newLine, options, errorCount) => {
+    changeSubject.next({ diagnostic, newLine, options, errorCount });
+  };
   ts.createWatchProgram(host);
-  return new Promise(() => {});
+  return changeSubject.asObservable();
 }
 
 function normalizeOptions(